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

HRID 975646Notes

Reaction equation

[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.CC(C)([O-])C.[K+].[CH2:12]([O:15][C:16]([N:18]1[CH2:22][C@H:21]([O:23][Si:24]([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25])[CH2:20][C@H:19]1[CH2:31][CH2:32]OS(C)(=O)=O)=[O:17])[CH:13]=[CH2:14].O>CN(C)C=O.C(OCC)(=O)C>[CH2:12]([O:15][C:16]([N:18]1[CH2:22][C@H:21]([O:23][Si:24]([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:25])[CH3:26])[CH2:20][C@H:19]1[CH2:31][CH2:32][N:1]1[CH:5]=[CH:4][N:3]=[CH:2]1)=[O:17])[CH:13]=[CH2:14]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of imidazole (1.52 in N,N-dimethylformamide (70 ml) were added potassium t-butoxide (2.51 g) and a solution of (2R,4R)-1-allyloxycarbonyl-2-(2-methanesulfonyloxyethyl)-4-(t-butyldimethylsilyloxy)pyrrolidine (8.3 g) in N,N-dimethylformamide (13 ml) at ambient temperature with stirring, and the mixture was stirred at about 60° C. for 1 hour. The reaction mixture was cooled with ice-cooling, and water and ethyl acetate were added thereto. After separation, the organic layer was washed with brine, dried over anhydrous magnesium sulfate and evaporated in vacuo. The resulting residue was purified by silica gel chromatography eluting with a mixture of chloroform and methanol (10:0.3, V/V) to give (2R,4R)-1-allyloxycarbonyl-2-[2-(imidazol-1-yl)ethyl]-4-(t-butyldimethylsilyloxy)pyrrolidine (11.11 g).

Workup

temperatureThe reaction mixture was cooled with ice-
temperaturecooling
customAfter separation
washthe organic layer was washed with brine
dry with materialdried over anhydrous magnesium sulfate
customevaporated in vacuo
customThe resulting residue was purified by silica gel chromatography
washeluting with a mixture of chloroform and methanol (10:0.3, V/V)

Sources & evidence

ORD record: ord-521a718c276946819a1ac5b48f0d1c36
Source dataset: uspto-grants-1997_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05608056

Reaction notes

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