Category: 18881-17-9

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.18881-17-9,(S)-(1,2,3,4-Tetrahydroisoquinolin-3-yl)methanol,as a common compound, the synthetic route is as follows.,18881-17-9

To an ice cooled solution of 5-bromo-2-(3-(ethoxycarbonyl)-5-methyl-lH-pyrazol-l-yl)benzoic acid (45.0 g, 127.8 mmol) in DCM (450 mL) were added (5)-(l ,2,3,4-tetrahydroisoquinolin-3-yl)methanol (20.8 g, 102.27 mmol), HATU (72.7 g, 191.2 mmol), DIPEA (55.7 mL, 319.6 mmol) followed by stirring at RT for 12h. The reaction mixture was diluted with DCM (750 mL), washed with water (500 mL), brine (100 mL), dried over sodium sulphate and concentrated invacuo. The residue was purified on silica gel (100-200 mesh) to afford the the title compound as a liquid 50 g (79%). Rf = 0.44 (55 % EtOAc in hexane); NMR (400 MHz, DMSO-d6): delta 8.00 – 7.40 (m, 3H), 7.30 – 7.00 (m, 4H), 6.80 – 6.40 (m, 1H), 5.10 – 3.80 (m, 7H), 3.50 – 2.40 (m, 3H), 2.40 – 2.10 (m, 3H), 1.30 – 1.00 (m, 3H); ES-MS: m/z 498.2 (M+H).

18881-17-9 (S)-(1,2,3,4-Tetrahydroisoquinolin-3-yl)methanol 776757, aisoquinoline compound, is more and more widely used in various fields.

Reference£º
Patent; NOVARTIS AG; FORD, Daniel; PORTER, John Robert; VISSER, Michael Scott; YUSUFF, Naeem; WO2013/96051; (2013); A1;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

18881-17-9, (S)-(1,2,3,4-Tetrahydroisoquinolin-3-yl)methanol is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

18881-17-9, This compound is obtained using a protocol from the literature (R. B. Kawthekar et al. South Africa Journal of Chemistry 63, 195, 2009) starting from 15 g of (3S)-1,2,3,4-tetrahydroisoquinolin-3-ylmethanol (91.9 mmol) in the presence of benzyl chloroformate and triethylamine in solution in dichloromethane. After purification over silica gel (petroleum ether/AcOEt gradient), the title compound is obtained in the form of an oil. (0132) 1H NMR: delta (300 MHz; DMSO-d6; 300K): 7.33 (m, 5H, aromatic Hs, O-benzyl); 7.15 (s, 4H, aromatic Hs, H tetrahydroisoquinoline); 5.13 (s, 2H, CH2-Ph); 4.73 (d, 1H, H tetrahydroisoquinoline); 4.47 (m, H, CH2OH); 4.36 (m, 1H, H tetrahydroisoquinoline); 4.28 (d, 1H, H tetrahydroisoquinoline); 3.39 (dd, 1H, CH2OH); 3.23 (dd, 1H, CH2OH); 2.93 (dd, 1H, H tetrahydroisoquinoline); 2.86 (dd, 1H, H tetrahydroisoquinoline) (0133) IR: nu: OH: 3416 cm-1; nu: C-H: 754 cm-1

The synthetic route of 18881-17-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Les Laboratoires Servier; Vernails (R&D) Limited; CASARA, Patrick; LE DIGUARHER, Thierry; HENLIN, Jean-Michel; STARCK, Jeroeme-Benoit; LE TIRAN, Arnaud; DE NANTEUIL, Guillaume; GENESTE, Olivier; DAVIDSON, James Edward Paul; MURRAY, James Brooke; CHEN, I-Jen; WALMSLEY, Claire; GRAHAM, Christopher John; RAY, Stuart; MADDOX, Daniel; BEDFORD, Simon; (72 pag.)US2016/152599; (2016); A1;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

18881-17-9, (S)-(1,2,3,4-Tetrahydroisoquinolin-3-yl)methanol is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,18881-17-9

A 300-gallon reactor was charged with acetonitrile (236 kg) and THIC-alcohol (15 kg). The reaction mixture was cooled to less than 5 C. and methanesulfonic acid (39.9 kg) and sodium cyanate (17.8 kg) were added. The reaction mixture was allowed to warm to about 20 C. and held at this temperature for about 2 hours. HPLC analysis of the reaction mixture was performed to indicate that the reaction had gone to completion. The reaction mixture was diluted with toluene (104 kg) and cooled to less than 5 C. for 1 hour. The solid was isolated by filtration and the cake was washed with about 30 L of toluene. The wet cake was added back to a 100-gallon reactor containing 10.1 kg of concentrated HCl in 150 L of water. An in-process HPLC analysis showed that the reaction mixture contained no impurities greater than 1%. The reaction mixture was filtered to remove particulate matter. Then the upper toluene layer was removed and discarded. The aqueous layer was cooled to less than 5 C. and the pH adjusted to 10.5 by carefully adding 20% aqueous sodium hydroxide. The mixture was stirred for 1 hour then the solid was collected by filtration. The wet cake was slurry washed with water (50 L) and refiltered. The product was dried in vacuo at 40 C. to yield 14.79 kg of product, which was found to be 98.77% pure by HPLC assay.

18881-17-9 (S)-(1,2,3,4-Tetrahydroisoquinolin-3-yl)methanol 776757, aisoquinoline compound, is more and more widely used in various fields.

Reference£º
Patent; Choi, Yong-Moon; Kim, Min Woo; US2005/80268; (2005); A1;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.18881-17-9,(S)-(1,2,3,4-Tetrahydroisoquinolin-3-yl)methanol,as a common compound, the synthetic route is as follows.,18881-17-9

Compound 2 (5.3 g, 16.47 mmol) and (S)-(1,2,3,4-tetrahydroisoquinolin-3-yl)methanol (2.96 g, 18.12 mmol) were dissolved in DCM (47.1 mL). The reactionmixture was cooled to 0 oc and TEA (3.44 mL, 24.71 mmol) was added dropwise underAr. The reaction mixture was then warmed to rt and was stirred overnight. The solutionwas concentrated and the crude product was purified by silica gel chromatography(EtOAc/hexanes, gradient, 0% to 80%) to obtain compound 3 (7.22 g, 16.10 mmol, 98% yield). LCMS = 5.482 min (8 min method). Mass observed (ESI+): 449.25 (M+H).

The synthetic route of 18881-17-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; IMMUNOGEN, INC.; MILLER, Michael, Louis; SHIZUKA, Manami; (163 pag.)WO2018/195243; (2018); A1;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.18881-17-9,(S)-(1,2,3,4-Tetrahydroisoquinolin-3-yl)methanol,as a common compound, the synthetic route is as follows.,18881-17-9

Step 2: Compound A2 (5.3 g, 16.47 mmol) and (S)-(1,2,3,4-tetrahydroisoquinolin-3- yl)methanol (2.96 g, 18.12 mmol) were dissolved in DCM (47.1 mL). The reaction mixture was cooled to 0 C and TEA (3.44 mL, 24.71 mmol) was added dropwise under Ar. The reaction mixture was then warmed to rt and was stirred overnight. The solution was concentrated and the crude product was purified by silica gel chromatography (EtOAc/hexanes, gradient, 0% to 80%) to obtain compound A3 (7.22 g, 16.10 mmol, 98% yield). LCMS = 5.482 mm (8 mm method). Mass observed (ESI): 449.25 (M+H).

18881-17-9 (S)-(1,2,3,4-Tetrahydroisoquinolin-3-yl)methanol 776757, aisoquinoline compound, is more and more widely used in various fields.

Reference£º
Patent; IMMUNOGEN, INC.; MILLER, Michael, Louis; SHIZUKA, Manami; CHARI, Ravi, V.J.; (312 pag.)WO2019/133652; (2019); A1;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

18881-17-9, (S)-(1,2,3,4-Tetrahydroisoquinolin-3-yl)methanol is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,18881-17-9

To an ice cooled solution of 5-bromo-2-(3-(ethoxycarbonyl)-5-methyl-lH-pyrazol-l-yl)benzoic acid (45.0 g, 127.8 mmol) in DCM (450 mL) were added (5)-(l ,2,3,4-tetrahydroisoquinolin-3-yl)methanol (20.8 g, 102.27 mmol), HATU (72.7 g, 191.2 mmol), DIPEA (55.7 mL, 319.6 mmol) followed by stirring at RT for 12h. The reaction mixture was diluted with DCM (750 mL), washed with water (500 mL), brine (100 mL), dried over sodium sulphate and concentrated invacuo. The residue was purified on silica gel (100-200 mesh) to afford the the title compound as a liquid 50 g (79%). Rf = 0.44 (55 % EtOAc in hexane); NMR (400 MHz, DMSO-d6): delta 8.00 – 7.40 (m, 3H), 7.30 – 7.00 (m, 4H), 6.80 – 6.40 (m, 1H), 5.10 – 3.80 (m, 7H), 3.50 – 2.40 (m, 3H), 2.40 – 2.10 (m, 3H), 1.30 – 1.00 (m, 3H); ES-MS: m/z 498.2 (M+H).

As the paragraph descriping shows that 18881-17-9 is playing an increasingly important role.

Reference£º
Patent; NOVARTIS AG; VISSER, Michael Scott; YUSUFF, Naeem; WO2013/96055; (2013); A1;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.18881-17-9,(S)-(1,2,3,4-Tetrahydroisoquinolin-3-yl)methanol,as a common compound, the synthetic route is as follows.,18881-17-9

To 50 mL dichloromethane solution containing (S)-3-hydroxymethy-1,2,3,4-tetrahydroisoquinoline (4.53 g, 27.75 mmol) was added di-tert-butyl dicarbonate (5.45 g, 25.0 mmol, 0.9 eq) and the reaction mixture was stirred for 2 hours until no gas bubbling was observed. The reaction mixture was washed with 0.5 N HCl (50 mL) followed by brine (50 mL) to remove the residual starting material. After drying wth MgSO4 and filtration , dichloromethane mixture was evaporated to yield crude (S)-N-tert-Butyloxycarbonyl-3-hydroxymethyl-1,2,3,4-tetrahydroisoquinoline. The crude N-tert-Butyloxycarbonyl-3-hydroxymethyl-1,2,3,4-tetrahydroisoquinoline was redissolved in 100 mL tetrahydrofuran. NaH (60%, 1.22 g) was added portion by portion to the solution at 0C and after 30 min stirring at room temperature, MeNCS (2.23 g) was added and the mixture was stirred for 2 h at rt. Brine (50 mL) was added to the mixture to quench the reaction and after evaporation of volatile in vacuo, it was extracted with dichloromethane (50mLx 2) and combined layer was dried (MgSO4), filtered, evaporated. The resulting material was chromatographed with hexane-EtOAc (4:1) mixture over SiO2 to provide 7.07 g-(81.8 %) of (S)-N-tert-butyloxycarbonyl-3-(N-Methyl-thiocarbamoyloxymethyl)-1,2,3,4-tetrahydroisoquinoline. This material was dissolved in THF(30 mL) and 10 mL conc. HCl was added to the solution. One hour later, 5 mL of conc, HCl was added and stirred another 1 h until the reaction is finished. The reaction mixture was diluted with 30 mL of water and volatile were evaporated. During the evaporation, desired product was precipitated as white solid. The solid was filtered and dried to yield the product as the hydrochloride salt (4.8 g). 1H-NMR (200 MHz, DMSO-d6) delta: 10.5-9.7 (m, 2H), 9.30 (s, 1H), 7.23 (s, 4H), 4.90 (m, 2H), 4.38 (s, 2H), 3.15-3.00 (m, 2H), 2.95 (d, 2H), 2.80 (1H)

As the paragraph descriping shows that 18881-17-9 is playing an increasingly important role.

Reference£º
Patent; SK Corporation; EP1149079; (2004); B1;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.18881-17-9,(S)-(1,2,3,4-Tetrahydroisoquinolin-3-yl)methanol,as a common compound, the synthetic route is as follows.,18881-17-9

Step 7: (R)-methyl 2-(tert-butoxycarbonylamino)-2-(2-((S)-3-(hydroxymethyl)-3,4- dihydroisoquinolin-2(lH)-yl)ethyl)-6-(4, 4, 5, 5-tetramethyl-l, 3 ,2-dioxaborolan-2-yl)hexanoate[0183] A solution of (R)-methyl 2-(tert-butoxycarbonylamino)-2-(2-oxoethyl)-6-(4,4,5,5- tetramethyl-l,3,2-dioxaborolan-2-yl)hexanoate (0.148 g, 0.358 mmol, 1.0 equiv.) and (S)- (l,2,3,4-tetrahydroisoquinolin-3-yl)methanol (0.088 g, 0.54 mmol, 1.5 equiv.) in 1,2- dichloroethane (0.34 mL, 0.5 M) was treated with sodium tnacetoxyborohydride (0.19 g, 0.90 mmol, 2.5 equiv) in one portion. After stirring for 1.5 h, the reaction mixture was quenched with saturated aqueous NaHC03 (1 mL) and stirred for an additional 5 min. The resulting mixture was added to a separatory funnel, diluted with saturated aqueous NaCl (5 mL) and extracted with dichloromethane (2 x 10 mL). The organic layer was dried over MgSC>4, filtered and concentration under reduced pressure. Purification by flash columnchromatography eluting with 5% methanol in chloroform gave (R)-methyl 2-(tert- butoxycarbonylamino)-2-(2-((S)-3-(hydroxymethyl)-3,4-dihydroisoquinolin-2(lH)-yl)ethyl)- 6-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)hexanoate as a pale yellow oil (0.187 g, 93%). Rf 0.52 (10% methanol in dichloromethane); 1H NMR (CDCI3, 300 MHz) delta 7.15 – 7.08 (m, 2 H), 7.07 – 6.98 (m, 2 H), 5.90 (s, 1 H), 3.78 (d, J = 16.2 Hz, 1 H), 3.70 (s, 3 H), 3.60 – 3.47 (m, 2 H), 3.04 – 2.93 (m, 1 H), 2.92 – 2.82 (m, 1 H), 2.71 – 2.60 (m, 1 H), 2.56 – 2.38 (m, 2 H), 2.37 – 2.23 (m, 1 H), 2.21 – 2.10 (m, 1 H), 1.77 -1.63 (m, 1 H), 1.42 (s, 9 H), 1.43 -1.26 (m, 3 H), 1.23 (s, 12 H), 1.22 – 1.16 (m, 1 H), 0.99 – 0.82 (m, 2 H), 0.74 (t, J = 7.5 Hz, 2 H); ESI-LCMS m/z calcd for C30H49BN2O7: expected 560.4; found 561.4 (M + H)+.

As the paragraph descriping shows that 18881-17-9 is playing an increasingly important role.

Reference£º
Patent; MARS, INCORPORATED; VAN ZANDT, Michael; GOLEBIOWSKI, Adam; JI, Min, Koo; WHITEHOUSE, Darren; RYDER, Todd; BECKETT, Paul; WO2011/133653; (2011); A1;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

18881-17-9, (S)-(1,2,3,4-Tetrahydroisoquinolin-3-yl)methanol is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,18881-17-9

Bis acid 9 (4.29 g, 9.2 mmol) was dissolved in dichloromethane (31 mL), and DIEA (4.8 mL, 27.6 mmol) was added followed by HATU (9.09 g, 23.9 mmol). Mixture was stirred for 30 minutes and (S)-(1,2,3,4-tetrahydro-isoquinolin-3-yl)-methanol (3.60 g, 22.1 mmol) was added at once. Reaction mixture was allowed to stir overnight, then washed with 0.5 M HCl, saturated NaHCO3 and concentrated to dryness. The residue was purified on 220 g silica Teledyne Isco column (05% MeOH in DCM). Evaporation of product containing fractions afforded 6.0 g of 10 (86% yield).1H NMR (500 MHz, DMSO-d6) = 7.77 (br. s., 2 H), 7.28 – 7.25 (m, 1 H), 7.24 – 7.16 (m, 8 H), 7.13 (br. s., 1 H), 6.98 (d, J = 7.8 Hz, 2 H), 5.33 (d, J = 16.1 Hz, 1 H), 5.01 – 4.88 (m, 2 H), 4.34 – 4.25 (m, 8 H), 3.91 (s, 6 H), 3.43 (br. s., 2 H), 3.27 – 3.21 (m, 2 H), 3.00 (d, J = 1.5 Hz, 1 H), 3.03 – 2.97 (m, 1 H), 2.76 (d, J = 2.9 Hz, 1 H), 2.29 (t, J = 6.1 Hz, 2 H). LC/MS: retention time 2.96 min. (ESI) C39H41N4O12 calculated for [M+H] + 757; found 757.

The synthetic route of 18881-17-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; CELLERANT THERAPEUTICS, INC.; JUNUTULA, Jagath R.; JAMMALAMADAKA, Vasu; ZHU, Jianyu; (229 pag.)WO2018/53552; (2018); A2;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.18881-17-9,(S)-(1,2,3,4-Tetrahydroisoquinolin-3-yl)methanol,as a common compound, the synthetic route is as follows.

18881-17-9, To a stirred solution of 2-(4-chloro-3-dibutylcarbamoyl-5-methyl-pyrazol-l-yl)-5- methoxy-benzoic acid (0.35 g, 0.82 mmol) and (S)-(l,2,3,4-tetrahydroisoquinolin-3-yl)methanol (0.13 g, 0.82 mmol) in dichloromethane (8 mL) under nitrogen atmosphere was added l-ethyl-3- (3-dimethylaminopropyl)carbodiimide (0.16 g, 0.82 mmol) and hydroxybenzotriazole (0.13 g, 0.82 mmol). The mixture was stirred at ambient temperature for 5 minutes. Triethylamine (0.34 mL, 2.5 mmol) was added to the mixture. The reaction was stirred for 60 hours at ambient temperature. The mixture was washed with water and purified by eluting through a silica gel column with a 10 to 100% ethyl acetate / heptane gradient to afford the title compound (21 mg, 4.5% yield). MS (ESI) [m/e, (M+H)+] = 567.3. XH NMR (400 MHz, chloroform-d) delta ppm 6.75 – 7.36 (m, 7 H), 4.13 – 5.41 (m, 4 H), 3.80 – 3.96 (m, 3 H), 2.51 – 3.71 (m, 8 H), 2.17 – 2.32 (m, 3 H), 1.48 – 1.68 (m, 4 H), 1.19 – 1.44 (m, 4 H), 0.70 – 0.97 (m, 6 H).

As the paragraph descriping shows that 18881-17-9 is playing an increasingly important role.

Reference£º
Patent; NOVARTIS AG; VISSER, Michael Scott; YUSUFF, Naeem; WO2013/96055; (2013); A1;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem