(2R,4R)-1-Allyloxycarbonyl-4-methylsulfonyloxy-2-(2-methylsulfonyloxyethyl) pyrrolidine → (2R,4R)-1-Allyloxycarbonyl-2-[2-(4-cyanoimidazol-1-yl) ethyl]-4-methanesulfonyloxypyrrolidine

HRID 975710Notes

Reaction equation

HRID 975710 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].[C:24]([C:26]1[N:27]=[CH:28][NH:29][CH:30]=1)#[N: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:29]1[CH:30]=[C:26]([C:24]#[N:25])[N:27]=[CH:28]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 178510437HCID 178510437, compound

Product 1

HCID 53735347(2R,4R)-1-Allyloxycarbonyl-2-[2-(4-cyanoimidazol-1-yl) ethyl]-4-methanesulfonyloxypyrrolidineYield 39.4%

Procedure

(2R,4R)-1-Allyloxycarbonyl-4-methanesulfonyloxy-2-(2methanesulfonyloxyethyl)pyrrolidine (36.1 g) was reacted with 4-cyanoimidazole (10.0 g) and potassium t-butoxide (12.0 g) in substantially the same manner as Preparation 10-3) to give (2R,4R)-1-allyloxycarbonyl-2-[2-(4-cyanoimidazol-1-yl)ethyl]-4-methanesulfonyloxypyrrolidine (14.1 g) as a yellow paste.

Workup

  1. customas Preparation 10-3)

Sources & evidence

ORD record
ord-302b91312e0b4d9baea57427ec65e251
Source dataset
uspto-grants-1997_03
Patent number
US05608056

Reaction notes

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