Dimethyl Sulfoxide → tert-Butyl 3-oxo-2-phenylpiperidine-1-carboxylate

HRID 1107274Notes

Reaction equation

C(Cl)(=O)C(Cl)=O.CS(C)=O.[C:11]([O:15][C:16]([N:18]1[CH2:23][CH2:22][CH2:21][CH:20]([OH:24])[CH:19]1[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:17])([CH3:14])([CH3:13])[CH3:12].C(N(CC)CC)C>ClCCl>[C:11]([O:15][C:16]([N:18]1[CH2:23][CH2:22][CH2:21][C:20](=[O:24])[CH:19]1[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:17])([CH3:14])([CH3:12])[CH3:13]

Participants

Conditions

Temperature: -60 °C

Procedure

To a cooled (-60° C.) solution of oxalyl chloride (0.68 ml, 7.8 mmol) in dichloronmethane (17 ml) was added dimethyl sulphoxide (0.69 ml, 9.8 mmol) for 10 minutes before addition of (±)1-tert-butoxycarbonyl-3-hydroxy-2-phenylpiperidine (1.8 g, 6.5 mmol; prepared by the method described in European Patent Specification number 0 528 495-A) in dichloromethane (7 ml). The solution was stirred at -60° C. for 20 minutes, warmed to -30° C. and triethylamine (2.5 ml) added. The solution was warmed to room temperature then was washed with ice cold 10% aqueous citric acid solution (40 ml, twice), water and dried (MgSO4). After evaporation the residue was purified by chromatography on silica gel (eluting with hexane containing an increasing proportion of ethyl acetate up to 20%) to give the title compound.

Workup

customprepared by the method
temperaturewarmed to -30° C.
temperatureThe solution was warmed to room temperature
washthen was washed with ice cold 10% aqueous citric acid solution (40 ml
dry with materialtwice), water and dried (MgSO4)
customAfter evaporation the residue
customwas purified by chromatography on silica gel (
washeluting with hexane containing an increasing proportion of ethyl acetate up to 20%)

Sources & evidence

ORD record: ord-7bfb5fe95396445f8219e89207c58322
Source dataset: uspto-grants-2000_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06060469

Reaction notes

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