Dimethyl Sulfoxide → (2S)-1-benzoylpyrrolidin-2-al
Reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[C:11]([N:19]1[CH2:23][CH2:22][CH2:21][C@H:20]1[CH2:24][OH:25])(=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(CC)CC)C>C(Cl)Cl.O>[C:11]([N:19]1[CH2:23][CH2:22][CH2:21][C@H:20]1[CH:24]=[O:25])(=[O:18])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1Participants
Conditions
- Temperature
- -70 °C
Procedure
A solution of DMSO (27.9 ml) in methylene chloride (50 ml) was added to a solution of oxalyl chloride (16.4 ml) in methylene chloride (300 ml) which was cooled to -70° C. A solution of (2S)-1-benzoylpyrrolidine-2-methanol (24.1 g) in methylene chloride (120 ml) was added dropiwise to the solution at -70° C. The mixture was stirred for 30 mins. Triethylamine (89.5 ml) was added dropwise to the reaction solution at -70° C. The mixture was stirred for 50 mins at the same temperature, and then rised to 0° C. gradually. Water was added to the solution. The mixture was extracted with methylene chloride. The extract was washed, dried, and evaporated. The residue was purified by column chromatography on silica gel (hexane-EtOAc) to give the title compound (23.7 g) having the following physical data:
Workup
- stirringThe mixture was stirred for 50 mins at the same temperature
- customrised to 0° C.
- extractionThe mixture was extracted with methylene chloride
- washThe extract was washed
- customdried
- customevaporated
- customThe residue was purified by column chromatography on silica gel (hexane-EtOAc)
Sources & evidence
- ORD record
- ord-acf436e7271d4b659fd7d1e0b8df29cd
- Source dataset
- uspto-grants-1991_10
- Patent number
- US05053414
Reaction notes
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