Dimethyl Sulfoxide → (2S)-5-allyloxycarbonylimino-2-formyl-1-methylpyrrolidine
Reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH2:11]([O:14][C:15]([N:17]=[C:18]1[N:22]([CH3:23])[C@H:21]([CH2:24][OH:25])[CH2:20][CH2:19]1)=[O:16])[CH:12]=[CH2:13].C(N(CC)CC)C>ClCCl>[CH2:11]([O:14][C:15]([N:17]=[C:18]1[N:22]([CH3:23])[C@H:21]([CH:24]=[O:25])[CH2:20][CH2:19]1)=[O:16])[CH:12]=[CH2:13]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
To a solution of oxalyl chloride (0.52 ml) in dichloromethane (15 ml) was added dropwise dimethyl sulfoxide (0.60 ml) at -78° C. After stirring at -78° C. for 10 minutes, to the mixture was added dropwise a solution of (2S)-5-allyloxycarbonylimino-2-hydroxymethyl-1-methylpyrrolidine (0.63 g) in dichloromethane (10 ml). After stirring at -78° C. for 10 minutes, to the mixture was added dropwise triethylamine (2.1 ml) and the resulting mixture was allowed to warm to 0° C. The mixture was washed with water and brine, dried over magnesium sulfate, and evaporated. The residue was chromatographed on silica gel eluting with a mixture of acetone and dichloromethane (1:4 V/V) to give (2S)-5-allyloxycarbonylimino-2-formyl-1-methylpyrrolidine (0.46 g).
Workup
- stirringAfter stirring at -78° C. for 10 minutes, to the mixture
- temperatureto warm to 0° C
- washThe mixture was washed with water and brine
- dry with materialdried over magnesium sulfate
- customevaporated
- customThe residue was chromatographed on silica gel eluting with a mixture of acetone and dichloromethane (1:4 V/V)
Sources & evidence
- ORD record
- ord-d76dbee60845478f9e5664e5935736af
- Source dataset
- uspto-grants-1992_01
- Patent number
- US05081237
Reaction notes
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