反应详情

温度

-78 °C

Dissolve (3R)-5-bromo-3-({[tert-butyl(dimethyl)silyl]oxy}methyl)-3,4 dihydroisoquinoline (3.4 g, 9.59 mmol) in diethyl ether (160 mL). Cool to −78° C. on a dry ice-acetone bath. Add methylmagnesium chloride (26.9 mL, 80.6 mmol, 3M in THF) dropwise. Warm the reaction mixture slowly to room temperature and stir overnight. Quench with saturated ammonium chloride solution slowly. Extract with dichloromethane and dry over sodium sulfate, filter, and concentrate under reduced pressure. Combine with the crude product from a substantially same reaction run with 1.73 mmol of (3R)-5-bromo-3-({[tert-butyl(dimethyl)silyl]oxy}methyl)-3,4 dihydroisoquinoline. Purify the combined residues by silica gel chromatography eluting with ethyl acetate: hexanes (5-65% gradient) to give the title compound (3.78 g, 10.2 mmol). MS (m/z): 370 (M+1).

1. temperatureWarm the reaction mixture slowly to room temperature
2. customQuench with saturated ammonium chloride solution slowly
3. extractionExtract with dichloromethane
4. dry with materialdry over sodium sulfate
5. filtrationfilter
6. concentrationconcentrate under reduced pressure
7. customCombine with the crude product from a substantially same reaction
8. customPurify the combined residues by silica gel chromatography
9. washeluting with ethyl acetate