反应详情

A solution of (3S)-tert-butyl 3-(3-hydroxy-5-methyl-3-phenylhex-5-enylamino)piperidine-1-carboxylate (8.41 g, 21.65 mmol), triethylamine (4.53 mL, 1.5 equiv), pyridine (1.75 mL, 1 equiv) in dichloromethane (250 mL) was cooled to 0° C. Methyl chloroformate (3.35 mL, 2 equiv) was added slowly during a 10 min period. After 15 min, the mixture was warmed to it slowly and stirred 3 h. The mixture was diluted with ether (350 mL), washed with 5% aq HCl solution (2×30 mL), satd aq NaHCO3 solution (25 mL), brine (25 mL), and dried over Na2SO4. After filtration and concentration, the residue was purified by chromatography on a 120 g silica gel column, eluted with a 30-85% EtOAc in hexanes gradient, to afford (3S)-tert-butyl 3-((3-hydroxy-5-methyl-3-phenylhex-5-enyl)(methoxycarbonyl)amino)piperidine-1-carboxylate (5.80 g, 60%). LC-MS Method 1 tR=2.08 min., m/z 447 (M+1).

1. temperaturethe mixture was warmed to it slowly
2. washwashed with 5% aq HCl solution (2×30 mL), satd aq NaHCO3 solution (25 mL), brine (25 mL)
3. dry with materialdried over Na2SO4
4. filtrationAfter filtration and concentration
5. customthe residue was purified by chromatography on a 120 g silica gel column
6. washeluted with a 30-85% EtOAc in hexanes gradient