2,2,2-Trifluoroethanol → (2S,4R)-1-tert-Butyl 2-methyl 4-(4-(2,2,2-trifluoroethoxy)-2-(trifluoromethyl)phenylsulfonyl)pyrrolidine-1,2-dicarboxylate

HRID 1697594Notes

Reaction equation

HRID 1697594 reaction equation
[CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][C@@H:8]([S:10]([C:13]2[CH:18]=[CH:17][C:16](F)=[CH:15][C:14]=2[C:20]([F:23])([F:22])[F:21])(=[O:12])=[O:11])[CH2:7][N:6]1[C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[O:4].[F:31][C:32]([F:36])([F:35])[CH2:33][OH:34].C(=O)([O-])[O-].[Cs+].[Cs+]>>[CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][C@@H:8]([S:10]([C:13]2[CH:18]=[CH:17][C:16]([O:34][CH2:33][C:32]([F:36])([F:35])[F:31])=[CH:15][C:14]=2[C:20]([F:21])([F:22])[F:23])(=[O:12])=[O:11])[CH2:7][N:6]1[C:24]([O:26][C:27]([CH3:29])([CH3:30])[CH3:28])=[O:25])=[O:4]

Participants

4

Reactant 3

HCID 64092,2,2-TrifluoroethanolHCID 10796Cesium carbonateHCID 66771094(2S,4R)-1-tert-butyl 2-methyl 4-(4-fluoro-2-(trifluoromethyl)phenylsulfonyl)pyrrolidine-1,2-dicarboxylate

Product 1

HCID 86646837(2S,4R)-1-tert-Butyl 2-methyl 4-(4-(2,2,2-trifluoroethoxy)-2-(trifluoromethyl)phenylsulfonyl)pyrrolidine-1,2-dicarboxylate

Procedure

In analogy to the procedure described in example 306, (2S,4R)-4-(4-fluoro-2-trifluoromethyl-benzenesulfonyl)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (example 208 c) was treated with 2,2,2-trifluoroethanol and cesium carbonate to give a mixture of the title compound and starting material as yellow oil. MS (ESI): m/z=436.1 [M+H]+.

Workup

  1. customto give

Sources & evidence

ORD record
ord-7b3250aa66124694939c9eb084d4c0cb
Source dataset
uspto-grants-2012_04
Patent number
US08163793B2

Reaction notes

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