反应详情

To the solution of (S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-7-methyl-2-oxo-1,2-dihydroquinolin-6-yl)ethyl pivalate (8J) (16 mg, 0.03 mmol) in DMF (1 mL) was added sodium hydride (7 mg, 60% oil, 0.17 mmol). The mixture was stirred for 30 minutes, and benzyl bromide (64, 0.05 mmol) was added. The mixture was stirred another 90 minutes, and was quenched with water, and left for 12 hours. The mixture was extracted with ethyl acetate, and the organic layer was washed with water and brine, and dried over sodium sulfate. Concentration and purification by flash column chromatography (hexanes/EtOAc) gave (S)-2-(2-(benzyloxy)-5-(4-chlorophenyl)-7-methylquinolin-6-yl)-2-tert-butoxyethanol (3.1 mg). LCMS-ESI+ (m/z): [M-FH]+ calcd for C29H30ClNO3: 476.2. Found: 476.1. (S)-1-Benzyl-6-(1-tert-butoxy-2-hydroxyethyl)-5-(4-chlorophenyl)-7-methylquinolin-2(1H)-one was also isolated 6.1 mg LCMS-ESI+ (m/z): [M+H]+ calcd for LCMS-ESI+ (m/z): [M+H]+ calcd for C29H31ClNO3: 476.2. Found: 476.2.

1. stirringThe mixture was stirred another 90 minutes
2. customwas quenched with water
3. waitleft for 12 hours
4. extractionThe mixture was extracted with ethyl acetate
5. washthe organic layer was washed with water and brine
6. dry with materialdried over sodium sulfate
7. concentrationConcentration and purification by flash column chromatography (hexanes/EtOAc)