2,2,2-Trifluoroethanol → HCID 86762436, compound

HRID 1025330Notes

Reaction equation

HRID 1025330 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](F)[CH:5]=[CH:4][C:3]=1[S:9]([C@H:12]1[CH2:16][N:15]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C@H:14]([C:24]([O:26][CH3:27])=[O:25])[CH2:13]1)(=[O:11])=[O:10].[F:28][C:29]([F:33])([F:32])[CH2:30][OH:31].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C(=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([O:31][CH2:30][C:29]([F:33])([F:32])[F:28])[CH:5]=[CH:4][C:3]=1[S:9]([C@H:12]1[CH2:16][N:15]([C:17]([O:19][C:20]([CH3:21])([CH3:22])[CH3:23])=[O:18])[C@H:14]([C:24]([O:26][CH3:27])=[O:25])[CH2:13]1)(=[O:11])=[O:10]

Participants

5

Reactant 3

HCID 64092,2,2-TrifluoroethanolHCID 10796Cesium carbonateHCID 66771935HCID 66771935, compound

Product 1

HCID 86762436HCID 86762436, compoundYield 53.2%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

Under an atmosphere of argon, (2S,4R)-1-tert-butyl 2-methyl 4-(2-chloro-4-fluorophenylsulfonyl)pyrrolidine-1,2-dicarboxylate ([prepared in analogy to General Procedure C, steps C1-C3, using 2-chloro-4-fluorothiophenol in step C2] 1.5 g, 1.0 eq.) was combined with N,N-dimethylacetamide (15 ml) to give a light yellow solution. 2,2,2-Trifluoroethanol (854 mg, 617 μl, 8.53 mmol, Eq: 2.4) and cesium carbonate (2.09 g, 6.4 mmol, Eq: 1.8) were added. The reaction mixture was stirred over night at RT. The crude reaction mixture was concentrated in vacuo. The crude material was purified by flash chromatography (silica gel, 50 g, 0% to 50% ethyl acetate in heptane) to yield the title compound as a white foam (0.95 g, 53.2%, MS (m/e)=502.09 [M+H+]).

Workup

  1. customto give a light yellow solution
  2. customThe crude reaction mixture
  3. concentrationwas concentrated in vacuo
  4. customThe crude material was purified by flash chromatography (silica gel, 50 g, 0% to 50% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-c6d4a750ff3841d19a8ba39f38186981
Source dataset
uspto-grants-2014_05
Patent number
US08729061B2

Reaction notes

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