反应详情

A mixture of 1-chloro-5-methyl-3-phenylhex-5-en-3-ol (5.16g, 23mmol), (S)-tert-butyl 3-aminopiperidine-1-carboxylate (6.9 g, 1.5 equiv), KI (4.0 g, 1.05 equiv), K2CO3 (4.77 g, 1.5 equiv) were mixed with acetonitrile (100 mL) and heated to reflux for 20 h. The mixture was filtered through a pad of Celite, concentrated and purified by chromatography on a 120 g silica gel column, eluted with a 0-10% methanol in CH2Cl2 gradient, to afford (3S)-tert-butyl 3-(3-hydroxy-5-methyl-3-phenylhex-5-enylamino)piperidine-1-carboxylate (8.41 g, 94% yield). LC-MS Method 1 tR=1.56 min., m/z 389 (M+1).

1. temperatureheated
2. temperatureto reflux for 20 h
3. filtrationThe mixture was filtered through a pad of Celite
4. concentrationconcentrated
5. custompurified by chromatography on a 120 g silica gel column
6. washeluted with a 0-10% methanol in CH2Cl2 gradient