反应详情

A solution of ethyl 4-(4-acetamidopiperidin-1-yl)benzoate (0.123 g, 0.42 mmol) in CH2Cl2 (10 mL) under nitrogen at −78° C. was treated with DIBAL-H (1.0M in hexanes, 0.950 mL, 0.95 mmol) dropwise, via a syringe. After 20 minutes, the mixture was warmed to room temperature, stirred for 1 hour, and quenched with 10% Rochelle's salt. After stirring for 10 minutes, CH2Cl2 (50 mL) was added, and the stirring was continued for 15 additional minutes. The layers were separated and the aqueous phase was extracted with CH2Cl2 (50 mL) and ethyl acetate (50 mL). The combined organic phases were dried (MgSO4), filtered, concentrated, and purified by flash chromatography on silica gel, eluting with 100% ethyl acetate to 10% MeOH/ethyl acetate to afford N-(1-(4-(hydroxymethyl)phenyl)piperidin-4-yl)acetamide as a white solid (0.025 g, 24%).

1. customquenched with 10% Rochelle's salt
2. stirringAfter stirring for 10 minutes
3. additionCH2Cl2 (50 mL) was added
4. customThe layers were separated
5. extractionthe aqueous phase was extracted with CH2Cl2 (50 mL) and ethyl acetate (50 mL)
6. dry with materialThe combined organic phases were dried (MgSO4)
7. filtrationfiltered
8. concentrationconcentrated
9. custompurified by flash chromatography on silica gel
10. washeluting with 100% ethyl acetate to 10% MeOH/ethyl acetate