反应详情

To a solution of 4-tert-butoxycarbonylaminomethylpiperidine (3.62 g, 16.9 mmol) in dichloromethane (100 mL) was added 4-formylpiperidine-1-carboxylic acid methyl ester (2.89 g, 16.9 mmol) and acetic acid (0.96 mL). The mixture was stirred at room temperature for 10 min prior to the addition of sodium triacetoxyborohydride (5.4 g, 25.5 mmol). The final mixture was stirred at room temperature for 1 h. The reaction was terminated by adding saturated sodium bicarbonate solution (50 mL). The mixture was extracted with dichloromethane (100 mL), and the organic layer was dried over MgSO4. Evaporation of the organic solution afforded a pale yellow oily residue. It was purified by flash silica column chromatography (CH2Cl2 to 5% MeOH/CH2Cl2), yielding the title intermediate (4.4 g). (m/z): [M+H]+ calcd for C19H35N3O4 370.27. found 370.5.

1. customThe reaction was terminated
2. additionby adding saturated sodium bicarbonate solution (50 mL)
3. extractionThe mixture was extracted with dichloromethane (100 mL)
4. dry with materialthe organic layer was dried over MgSO4
5. customEvaporation of the organic solution
6. customafforded a pale yellow oily residue
7. customIt was purified by flash silica column chromatography (CH2Cl2 to 5% MeOH/CH2Cl2)