反应详情

In a dry ice-acetone bath under an argon atmosphere, a solution of 1.0 M methyllithium in diethyl ether (16.2 mL) was added dropwise to a solution of ethyl 2-benzyl-1,2,3,4-tetrahydroisoquinoline-1-carboxylate (1.99 g) in THF (20 mL) over 15 minutes. The reaction liquid was stirred in a dry ice-acetone bath for 0.5 hours and then further stirred in an ice bath for 1 hour. The reaction liquid was cooled again in the dry ice-acetone bath, and a solution of 1.04 M methyllithium in diethyl ether (3.24 mL) was added thereto. The reaction liquid was stirred in the dry ice-acetone bath for 0.5 hours and then stirred in the ice bath for 1 hour. Water was added to the reaction liquid, followed by extraction with EtOAc. The extract was washed with saturated brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane-EtOAc) to obtain 2-(2-benzyl-1,2,3,4-tetrahydroisoquinolin-1-yl)propan-2-ol (1.27 g).

1. customThe reaction liquid
2. stirringfurther stirred in an ice bath for 1 hour
3. customThe reaction liquid
4. customThe reaction liquid
5. extractionfollowed by extraction with EtOAc
6. washThe extract was washed with saturated brine
7. dry with materialdried over magnesium sulfate
8. filtrationfiltered
9. concentrationconcentrated under reduced pressure
10. customThe resulting residue was purified by silica gel column chromatography (hexane-EtOAc)