Imidazole → (2R,4R)-1-allyloxycarbonyl-2-[2-(imidazol-1-yl)ethyl]-4-(methanesulfonyloxy)pyrrolidine

HRID 975656Notes

Reaction equation

HRID 975656 reaction equation
[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@H:10]([O:12][S:13]([CH3:16])(=[O:15])=[O:14])[CH2:9][C@H:8]1[CH2:17][CH2:18]OS(C)(=O)=O)=[O:6])[CH:2]=[CH2:3].[NH:24]1[CH:28]=[CH:27][N:26]=[CH:25]1.CC(C)([O-])C.[K+].O>CN(C)C=O>[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@H:10]([O:12][S:13]([CH3:16])(=[O:14])=[O:15])[CH2:9][C@H:8]1[CH2:17][CH2:18][N:24]1[CH:28]=[CH:27][N:26]=[CH:25]1)=[O:6])[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 15537962(2R,4R)-1-Allyloxycarbonyl-4-methylsulfonyloxy-2-(2-methylsulfonyloxyethyl) pyrrolidineHCID 23665647Potassium tert-butoxide

Product 1

HCID 54297291(2R,4R)-1-allyloxycarbonyl-2-[2-(imidazol-1-yl)ethyl]-4-(methanesulfonyloxy)pyrrolidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (2R,4R)-1-allyloxycarbonyl-4-methanesulfonyloxy-2-(2-methanesulfonyloxyethyl)pyrrolidine (5.35 g) in N,N-dimethylformamide (54 ml) were added imidazole (1.18 g) and potassium t-butoxide (1.78 g) with stirring under ice-cooling. The mixture was stirred at 40°-45° C. for 40 minutes. The reaction mixture was poured into water (100 ml) and extracted with dichloromethane (80 ml). The extract was washed in turn with water (50 ml) and 10% aqueous sodium chloride (50 ml), dried over anhydrous magnesium sulfate and evaporated in vacuo to give (2R,4R)-1-allyloxycarbonyl-2-[2-(imidazol-1-yl)ethyl]-4-methanesulfonyloxypyrrolidine.

Workup

  1. temperaturecooling
  2. stirringThe mixture was stirred at 40°-45° C. for 40 minutes
  3. extractionextracted with dichloromethane (80 ml)
  4. washThe extract was washed in turn with water (50 ml) and 10% aqueous sodium chloride (50 ml)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-bd22d8f5b7684b98ba9bb434dd3f159e
Source dataset
uspto-grants-1997_03
Patent number
US05608056

Reaction notes

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