反应详情

Methanesulfonyl chloride (44 μL, 0.56 mmol) in dichloromethane (10 mL) was added slowly to a stirred, cooled (0° C.) solution of 1,1-dimethylethyl 4,4-bis(hydroxymethyl)-1-piperidinecarboxylate (Description 67, 140 mg, 0.56 mmol) and triethylamine (95 μL, 0.68 mmol) in dichloromethane (50 mL). The mixture was allowed to warm to room temperature and stirred for 16 hours. Water (10 mL) was added and the layers were separated. The aqueous layer was extracted with dichloromethane (2×40 mL), the combined organic fractions were dried (MgSO4) and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluting with isohexane/EtOAc (80:20 increasing to 0:100), to give the title compound (98 mg, 54%). m/z (ES+) 324 (M+1).

1. customthe layers were separated
2. extractionThe aqueous layer was extracted with dichloromethane (2×40 mL)
3. dry with materialthe combined organic fractions were dried (MgSO4)
4. customthe solvent was evaporated under reduced pressure
5. customThe residue was purified by flash column chromatography on silica gel
6. washeluting with isohexane/EtOAc (80:20 increasing to 0:100)