反应详情

Acetic acid (1 ml) was added dropwise to a solution of N-tert-butoxycarbonyl-4-piperidone (9.4 g), 1-(2-amino-phenyl)-ethanol (4.3 g) and sodium cyanoborohydride (10 g) in dichloromethane and the mixture stirred at room temperature overnight. The mixture was partitioned between ethyl acetate and water, the organics separated and washed with aqueous sodium hydrogencarbonate solution, water, dried, and evaporated under reduced pressure. The crude product was dissolved in tetrahydrofuran (100 ml) and N,N-diisopropylethylamine (23 ml), cooled to 0° C., then triphosgene (4.3 g) added. The mixture was warmed to room temperature and stirred overnight. The mixture was partitioned between ethyl acetate and water, the organics washed with water, dried and evaporated under reduced pressure. Purification was by chromatography eluting with 20% ethyl acetate/isohexane. Yield 1.4 g.

1. customThe mixture was partitioned between ethyl acetate and water
2. customthe organics separated
3. washwashed with aqueous sodium hydrogencarbonate solution, water
4. customdried
5. customevaporated under reduced pressure
6. dissolutionThe crude product was dissolved in tetrahydrofuran (100 ml)
7. temperatureN,N-diisopropylethylamine (23 ml), cooled to 0° C.
8. additiontriphosgene (4.3 g) added
9. temperatureThe mixture was warmed to room temperature
10. stirringstirred overnight
11. customThe mixture was partitioned between ethyl acetate and water
12. washthe organics washed with water
13. customdried
14. customevaporated under reduced pressure
15. customPurification
16. washeluting with 20% ethyl acetate/isohexane