反应详情

A solution of tert-butyl 4-methyl-5-oxohexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate (10.7 g, 44.7 mmol) and benzyl amine (7.67 g, 71.5 mmol) in 1,2-dichloroethane (250 mL) was stirred at room temperature for 2 h. Anhydrous magnesium sulfate (20 g, 166 mmol) was added. The resultant suspension was stirred at room temperature for additional 2 h. Sodium triacetoxyborohydride (18.95 g, 89 mmol) was added. After 60 h at room temperature, the mixture was quenched with saturated sodium bicarbonate (100 mL) and extracted with ethyl acetate (3×150 mL). The combined organic extracts were washed with water, brine, dried (MgSO4) and concentrated. Silica gel chromatography, eluting with 0-8% methanol in dichloromethane, gave tert-butyl 5-(benzylamino)-4-methylhexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate as a mixture of stereoisomers (13.2 g), which was taken to the next reaction without separation.

1. customthe mixture was quenched with saturated sodium bicarbonate (100 mL)
2. extractionextracted with ethyl acetate (3×150 mL)
3. washThe combined organic extracts were washed with water, brine
4. dry with materialdried (MgSO4)
5. concentrationconcentrated
6. washSilica gel chromatography, eluting with 0-8% methanol in dichloromethane