Methyl iodide → (2S,4R)-4-methanesulfonyloxy-1-methyl-2-(2-oxoimidazolidin-1-yl)carbonylpyrrolidine
Reaction equation
[CH3:1][S:2]([O:5][C@H:6]1[CH2:10][NH:9][C@H:8]([C:11]([N:13]2[CH2:17][CH2:16][NH:15][C:14]2=[O:18])=[O:12])[CH2:7]1)(=[O:4])=[O:3].[CH2:19](N(CC)CC)C.CI>CO.O1CCCC1>[CH3:1][S:2]([O:5][C@H:6]1[CH2:10][N:9]([CH3:19])[C@H:8]([C:11]([N:13]2[CH2:17][CH2:16][NH:15][C:14]2=[O:18])=[O:12])[CH2:7]1)(=[O:4])=[O:3]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 40 °C
Procedure
To a solution of (2S,4R)-4-methanesulfonyloxy-2-(2-oxoimidazolidin-1-yl)carbonylpyrrolidine (14.9 g) in a mixture of methanol (150 ml) and tetrahydrofuran (150 ml) were added triethylamine (32.5 ml) and methyl iodide (11.4 ml) and the mixture was stirred at 40° C. for 2 hours. The reaction mixture was evaporated in vacuo. The resulting residue was chromatographed on silica gel (600 g) eluting with a mixture of chloroform and methanol (9:1 V/V). The fractions containing the desired compound were collected and evaporated in vacuo to give a residue. The residue was washed with dichloromethane (100 ml). The resulting precipitates were collected and dried in vacuo to give (2S,4R)-4-methanesulfonyloxy-1-methyl-2-(2-oxoimidazolidin-1-yl)carbonylpyrrolidine (2.30 g).
Workup
- customThe reaction mixture was evaporated in vacuo
- customThe resulting residue was chromatographed on silica gel (600 g)
- washeluting with a mixture of chloroform and methanol (9:1 V/V)
- additionThe fractions containing the desired compound
- customwere collected
- customevaporated in vacuo
- customto give a residue
- washThe residue was washed with dichloromethane (100 ml)
- customThe resulting precipitates
- customwere collected
- customdried in vacuo
Sources & evidence
- ORD record
- ord-3fe55ca3ddbf4134af3ec084ae6a5b0a
- Source dataset
- uspto-grants-1990_05
- Patent number
- US04925838
Reaction notes
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