60518-41-4 7-Chloro-3,4-dihydroisoquinoline 19748121, aisoquinoline compound, is more and more widely used in various fields.
60518-41-4, 7-Chloro-3,4-dihydroisoquinoline is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,60518-41-4
Step 1: (lS)-7-Chloro-l-[5-(l,3-dioxolan-2-yl)-2-methyl-3-thienyl]-l,2,3,4- tetrahydroisoquinoline and (lR)-7-chloro-l-[5-(l,3-dioxolan-2-yI)-2-methyl-3-thienyl]-l,2,3,4- tetrahydroisoquinoline [00992] To a solution of 2-(4-bromo-5-methyl-2-thienyl)-l ,3-dioxolane (90.3 g, 362 mmol) in THF (500 mL) was added dropwise 2.50 M of n-BuLi ( 193 mL, 483 mmol) at -78 C under an atmosphere of N2, and the mixture was allowed to stir at -78C for 20 min. Another reaction vessel was charged with 7-chloro-3,4-dihydroisoquinoline (40 g, 242 mmol) and the contents were dissolved in THF ( 1.3L). To this solution was added dropwise BF3-Et20 (32.8 mL, 265.7 mmol) at -30C, and the solution was allowed to stir for 10 min. To this mixture was added dropwise the previous lithiated mixture via cannula and the resulting mixture was allowed to stir at -30C for 30 min. Then the reaction mixture was allowed to warm to 0C and stirred for 1 h. The reaction was quenched by addition of saturated aqueous NaHC03, and the mixture was extracted with EtOAc (500 mL x 3). The combined organic layers were washed with brine, dried over Na2S04, filtered, and concentrated in vacuo. The above procedure was perfomed on the same scale two additional times. The residues from all three procedures were then combined and purified by silica gel chromagraphy, eluting with a 85/15 to 0/100 pentane/EtOAc gradient to provide a yellow solid. The resulting solid was washed with pentane of to provide the racemic mixture (1 10 g, 45%) as a yellow solid. The racemic mixture was separated into the individual component enantiomers by chiral chromatography (SFC: CHIRALPAK AD 50x300mm with 35/65 0.1 % NH4OH in MeOH/C02, 200 mL/min, 10 MPa) to obtain 51.5 g (99.7% ee) of (lR)-7- chloro- l -[5-( l ,3-dioxolan-2-yl)-2-methyl-3-thienyl]- l ,2,3,4-tetrahydroisoquinoline as first elute (retention time 3.7 min, LCMS: (AA) M+ l 336.0) and 50.0g (99.7% ee) of (l S)-7-chloro- l -[5- ( l ,3-dioxolan-2-yl)-2-methyl-3-thienyl]-l ,2,3,4-tetrahydroisoquinoline as second elute (retention time 4.8 min, LCMS: (AA) M+l 336.0).
60518-41-4 7-Chloro-3,4-dihydroisoquinoline 19748121, aisoquinoline compound, is more and more widely used in various fields.
Reference£º
Patent; DUFFEY, Matthew O.; ENGLAND, Dylan; FREEZE, Scott; HU, Zhigen; LANGSTON, Steven, P.; MCINTYRE, Charles; MIZUTANI, Hirotake; ONO, Koji; XU, He; (684 pag.)WO2016/4136; (2016); A1;,
Isoquinoline – Wikipedia
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