Category: 18881-17-9

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

Compound 62 (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 dichloromethane (47.1 mL). The reaction mixture was cooled to0 C and triethylamine (3.44 mL, 24.71 mmol) was added dropwise under Ar. The reaction mixturewas then warmed to room temperature and was stirred overnight. The solution was concentratedand the crude product was purified by silica gel chromatography (ethyl acetate/hexanes, gradient,0% to 80%) to obtain compound 12 (7.22 g, 16.10 mmol, 98% yield).

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
Article; Reid, Emily E.; Archer, Katie E.; Shizuka, Manami; McShea, Molly A.; Maloney, Erin K.; Ab, Olga; Lanieri, Leanne; Wilhelm, Alan; Ponte, Jose F.; Yoder, Nicholas C.; Chari, Ravi V.J.; Miller, Michael L.; Bioorganic and Medicinal Chemistry Letters; vol. 29; 17; (2019); p. 2455 – 2458;,
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 A: Benzyl (3S)-3-(hydroxymethyl)-3,4-dihydro-1H-isoquinoline-2-carboxylate 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 by chromatography over silica gel using petroleum ether and ethyl acetate as eluants, the title product is obtained in the form of an oil. 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) 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; LE TIRAN, Arnaud; LE DIGUARHER, Thierry; STARCK, Jerome-Benoit; HENLIN, Jean-Michel; GUILLOUZIC, Anne-Francoise; DE NANTEUIL, Guillaume; GENESTE, Olivier; FEJES, Imre; TATAI, Janos; NYERGES, Miklos; DAVIDSON, James Edward Paul; MURRAY, James Brooke; CHEN, I-Jen; DURAND, Didier; US2015/31673; (2015); 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 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).

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; WO2013/96060; (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

Then, 2,4-dichloro-6-mophiholin-4-yl-[l,3,5]triazine (3.0 g, 12.8 mmol) thus obtained was dissolved in acetonitrile (50 ml), mixed with diisopropylethylamine (71.7 g, 12.8 mmol) and (_S)-l,2,3,4-tetrahydro-3- isoquinolinemethanol (2.1 g, 12.8 mmol) at room temperature, and stirred for 24 hours. The resulting mixture was diluted with ethyl acetate, and washed successively with water and saturated NaCl. The resulting organic layer was dried over anhydrous magnesium sulfate, and concentrated under a reduced pressure. The resulting residue was purified by column chromatography to obtain [2-(4-chloro-6-morpholin-4-yl-[l,3,5]triazin-2-yl)-l,2,3,4- tetrahydroisoqumolin-(35)-yl]-methanol (4.4 g, 95%).1H NMR (300 MHz, CDCl3) delta: 7.25-7.15 (4H, m), 5.13-5.01 (2H, m), 4.52 (IH, t, J=17.7Hz), 3.85 (4H, br), 3.73 (4H, br), 3.65-3.50 (2H, m), 3.09 (IH, dd, J=15.9Hz, 6.0Hz), 2.89 (IH, dt, J=13.1Hz 3.3Hz), 2.55 (IH, br).

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

Reference£º
Patent; AMOREPACIFIC CORPORATION; CRYSTALGENOMICS, INC.; INDUSTRY-ACADEMIC COOPERATION FOUNDATION, YONSEI UNIVERSITY of Yonsei University; WO2008/72850; (2008); 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 30.2g [(3S) – 1, 2, 3, 4-tetrahydrosquinoline-3-yl] methanol (185mmol) in 750 ml of methylene chloride is added in solution 91.71g toluene sulfonyl chloride (481mmol), then dropwise 122.3mLN, N, N-triethylamine (740mmol). Then the temperature of the reaction mixture is stirred for 20 hours. Furthermore, the dichloromethane is used for dilution, for sequentially 1MHCl solution, saturated NaHCO3solution, then washed with saturated NaCl solution until neutral. Then the organic phase through MgSO4drying, filtering, concentrated to dry. Then the obtained solid is dissolved in a minimum volume of methylene chloride, then adding cyclohexane to form precipitate. Then filtering out the precipitated, with cyclonexane washing. After drying, the title of the crystalline form of the product is obtained.

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; France Servier Pharmaceuticals; p, Casara; T, Le Diguaher; J-M, Henlin; J-B, Starck; A, Le Tiran; G, De Nanteuil; O, Geneste; J¡¤E¡¤P, Davidson; J¡¤B, Murray; I-J, Chen; C, Walmsley; C¡¤J, Graham; S, Ray; D, Maddox; S, Bedford; (116 pag.)CN105408321; (2016); A;,
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 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; FORD, Daniel; PORTER, John Robert; VISSER, Michael Scott; YUSUFF, Naeem; WO2013/96051; (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

Step A: Benzyl (3S)-3-(hydroxymethyl)-3,4-dihydro-1H-isoquinoline-2-carboxylate 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 by chromatography over silica gel using petroleum ether and ethyl acetate as eluants, the title product is obtained in the form of an oil. 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) IR: nu: OH: 3416 cm-1; nu: C-H: 754 cm-1

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

Reference£º
Patent; LE TIRAN, Arnaud; LE DIGUARHER, Thierry; STARCK, Jerome-Benoit; HENLIN, Jean-Michel; GUILLOUZIC, Anne-Francoise; DE NANTEUIL, Guillaume; GENESTE, Olivier; FEJES, Imre; TATAI, Janos; NYERGES, Miklos; DAVIDSON, James Edward Paul; MURRAY, James Brooke; CHEN, I-Jen; DURAND, Didier; US2015/31673; (2015); 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

Intermediate 116(5)-N,N-Dimethyl-2-((l,2 -tetrahydroisoquinolin-3-yl)methoxy)ethanamineIntermediate 116A: (5)-l-(3-(Hydroxymethyl)-3,4-dihydroisoquinolin-2(lH)- yl)ethanone[00362] To (S)-(l,2,3,4-tetrahydroisoquinolin-3-yl)methanol (Aldrich, 350 mg, 2.14 mmol) in EtOAc (4.3 mL) and MeOH (1.1 mL) was added Ac20 (243 mu, 2.57 mmol). The resulting reaction mixture was stirred at room temperature for 2 h. K2CO3 was then added to neutralize the AcOH, and the reaction mixture was filtered through a pad ofCELITE, washing with EtOAc. The filtrate was concentrated in vacuo to give the title compound (316 mg, 72%) as a white solid. lH NMR (CDCI3, 1.5: 1 mixture of amide rotamers) delta 7.26-7.10 (m, 4H), 5.17 (d, J= 18.0 Hz, 0.5H), 4.90 (dt, J= 5.1, 9.4 Hz, 0.5H), 4.66-4.44 (m, 1H), 4.39-4.23 (m, 1H), 3.66-3.55 (m, 1H), 3.55-3.45 (m, 1H), 3.14 (dd, J= 5.9, 16.3 Hz, 0.5H), 3.02 (dd, J= 6.2, 15.8 Hz, 0.5H), 2.92-2.76 (m, 1H), 2.27 (s, 1H), 2.24 (s, 2H); MS(ESI+) m/z 206.1 (M+H)+.

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

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; BORZILLERI, Robert M.; CAI, Zhen-wei; TEBBEN, Andrew J.; PEREZ, Heidi L.; ZHANG, Liping; SCHROEDER, Gretchen M.; WEI, Donna D.; WO2012/162365; (2012); 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, The experimental procedure used for this reaction was adapted from the literature.15 To a solution of (S)-3-hydroxymethyl-1,2,3,4-tetrahydroisoquinoline 4 (1.42 g, 8.70 mmol) in dioxane (20 mL) and water (10 mL) at 0 C, was added dropwise a solution of potassium hydrogen carbonate (4.30 g, 41.0 mmol) in water (10 mL) over 15 min followed by addition of CbzCl (1.63 g,9.50 mmol). The mixture was stirred for 1.5 h at 0 C and then atambient temperature for a further 1.5 hours. Completion of the reaction was monitored by TLC in hexane:ethyl acetate (60:40,Rf = 0.32). The solvent was removed under reduced pressure to afford the crude compound (S)-benzyl 3-(hydroxymethyl)-1,2,3,4-tetrahydroisoquinoline-2-carboxylate 5, which was purified by column chromatography using 0-40% ethyl acetate in hexane as the eluent to yield pure compound 5 as an oil. Yield1.85 g (74%). [alpha]D20 (c = 0.35, in CH2Cl2). IR numax/cm-1 = 3418, 3030,2945, 1676, 1415, 1345, 1219, 1119, 1027 and 741. NMR spectrumare reported for a mixture of two rotamers.20.21 1H NMR(400 MHz, CDCl3) delta = 2.83 (brd, 1H, J = 15.15 Hz), 3.04 (dd, 1H,J=6.08, 15.95 Hz) , 3.36-3.63 (m, 2H), 4.29-4.47 (m, 1H), 4.48-4.64(m, 1H), 4.70-4.95 (m, 1H), 5.19 (s, 2H) and 7.01-7.43 (m, 9H). TheOH proton was not observed. 13C NMR (100 MHz, CDCl3) delta =156.9, 136.4, 132.8, 132.5, 129.8, 128.8, 128.5, 128.0, 127.9, 127.8,127.0, 126.4, 126.0, 125.9, 67.4, 63.3, 52.3, 43.7 and 29.8.HRESI MS:m/z = 320.2159 [M+ Na]+ (calcd. for C18H19NNaO3 = 320.1257).

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

Reference£º
Article; Kawthekar, Rahul B.; Peters, Byron K.; Govender, Thavendran; Kruger, Hendrik G.; Maguire, Glenn E.M.; South African Journal of Chemistry; vol. 63; (2010); p. 195 – 198;,
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, This derivative is obtained using a literature protocol (RB et al Kawthekar South Africa Journal of Chemistry 63, 195, 2009) from 15 g of (35) – 1,2,3, 4- ttrahydiOisoquinolin-3-y nthanol (91.9 mmol) in the presence of benzyl chloroformate and triethylamine in dichloromethane solution.After purification on silica gel (petroleum ether / AcOEt gradient), the title product is obtained as an oil.

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

Reference£º
Patent; France Servier Pharmaceuticals; p, Casara; T, Le Diguaher; J-M, Henlin; J-B, Starck; A, Le Tiran; G, De Nanteuil; O, Geneste; J¡¤E¡¤P, Davidson; J¡¤B, Murray; I-J, Chen; C, Walmsley; C¡¤J, Graham; S, Ray; D, Maddox; S, Bedford; (116 pag.)CN105408321; (2016); A;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem