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

HRID 975705Notes

Reaction equation

HRID 975705 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[N:34]=[CH:35][NH:36][CH:37]=1)([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25].CC(C)([O-])C.[K+]>>[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:36]1[CH:37]=[C:33]([CH2:32][O:31][Si:24]([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:25])[CH3:26])[N:34]=[CH:35]1)=[O:6])[CH:2]=[CH2:3]

Participants

4

Reactant 3

HCID 15537962(2R,4R)-1-Allyloxycarbonyl-4-methylsulfonyloxy-2-(2-methylsulfonyloxyethyl) pyrrolidineHCID 23665647Potassium tert-butoxideHCID 178455170HCID 178455170, compound

Product 1

HCID 54108174(2R,4R)-1-allyloxycarbonyl-2-[2-{4-(t-butyldimethylsilyloxymethyl)-imidazol-1-yl}ethyl]-4-methanesulfonyloxypyrrolidineYield 136.7%

Procedure

(2R,4R)-1-Allyloxycarbonyl-4-methanesulfonyloxy-2-(2-methanesulfonyloxyethyl)pyrrolidine (13.2 g) was reacted with 4-(t-butyldimethylsilyloxymethyl)imidazol (8.30 g) and potassium t-butoxide (4.39 g) in substantially the same manner as Preparation 10-3) to give (2R,4R)-1-allyloxycarbonyl-2-[2-{4-(t-butyldimethylsilyloxymethyl)-imidazol-1-yl}ethyl]-4-methanesulfonyloxypyrrolidine (23.7 g) as a brown paste.

Workup

  1. customas Preparation 10-3)

Sources & evidence

ORD record
ord-bf9951c8193345b89a60d8dd74704e98
Source dataset
uspto-grants-1997_03
Patent number
US05608056

Reaction notes

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