(2R,4R)-1-Allyloxycarbonyl-4-methylsulfonyloxy-2-(2-methylsulfonyloxyethyl) pyrrolidine → (2R,4R)-1-allyloxycarbonyl-2-[2-(2-(t-butyldimethylsilyloxymethyl) imidazol-1-yl)ethyl]-4-methylsulfonyloxypyrrolidine

HRID 975672Notes

Reaction equation

HRID 975672 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].[Si:24]([O:31][CH2:32][C:33]1[NH:34][CH:35]=[CH:36][N:37]=1)([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25]>>[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:34]1[CH:35]=[CH:36][N:37]=[C:33]1[CH2:32][O:31][Si:24]([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:25])[CH3:26])=[O:6])[CH:2]=[CH2:3]

Participants

3

Reactant 2

HCID 15537962(2R,4R)-1-Allyloxycarbonyl-4-methylsulfonyloxy-2-(2-methylsulfonyloxyethyl) pyrrolidineHCID 217451052-(t-Butyldimethylsilyloxymethyl)imidazole

Product 1

HCID 54342959(2R,4R)-1-allyloxycarbonyl-2-[2-(2-(t-butyldimethylsilyloxymethyl) imidazol-1-yl)ethyl]-4-methylsulfonyloxypyrrolidineYield 91.2%

Procedure

(2R,4R)-1-Allyloxycarbonyl-4-methylsulfonyloxy-2-(2-methylsulfonyloxyethyl) pyrrolidine (28.8 g) and 2-(t-butyldimethylsilyloxymethyl)imidazole (18.1 g) were reacted in substantially the same manner as that of Preparation 10-3) to give (2R,4R)-1-allyloxycarbonyl-2-[2-(2-(t-butyldimethylsilyloxymethyl) imidazol-1-yl)ethyl]-4-methylsulfonyloxypyrrolidine (34.5 g) as a yellow paste.

Workup

  1. customof Preparation 10-3)

Sources & evidence

ORD record
ord-ff163d1367894ef8aa6adce3cf452e6c
Source dataset
uspto-grants-1997_03
Patent number
US05608056

Reaction notes

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