Trifluoroacetic acid → (2S,4R)-methyl 4-(2-chlorophenylsulfonyl)pyrrolidine-2-carboxylate

HRID 1025327Notes

Reaction equation

HRID 1025327 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([C@H:11]1[CH2:15][N:14](C(OC(C)(C)C)=O)[C@H:13]([C:23]([O:25][CH3:26])=[O:24])[CH2:12]1)(=[O:10])=[O:9].FC(F)(F)C(O)=O>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([C@H:11]1[CH2:15][NH:14][C@H:13]([C:23]([O:25][CH3:26])=[O:24])[CH2:12]1)(=[O:9])=[O:10]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66770853(2S,4R)-1-tert-butyl 2-methyl 4-(2-chlorophenylsulfonyl)pyrrolidine-1,2-dicarboxylate

Product 1

HCID 66770749(2S,4R)-methyl 4-(2-chlorophenylsulfonyl)pyrrolidine-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under an atmosphere of argon, (2S,4R)-1-tert-butyl 2-methyl 4-(2-chlorophenylsulfonyl)pyrrolidine-1,2-dicarboxylate (5.76 g, 14.3 mmol, Eq: 1.00) was combined with dichloromethane (35.0 ml) to give a light yellow solution. At 0° C., 2,2,2-trifluoroacetic acid (24.4 g, 16.5 ml, 214 mmol, Eq: 15.0) was added dropwise. The reaction was warmed up to room temperature and stirred for 3 h. The reaction mixture was evaporated to dryness. The crude material was dissolved in 100 ml dichloromethane, then extracted with 50 ml satd. Na2CO3 solution and 50 ml H2O. The aqueous layers were washed with 40 ml dichloromethane. The organic layer was dried over Na2SO4, filtered, and concentrated in vacuo. The title compound was obtained as a orange viscous oil (4.02 g, 92.8%, MS (m/e)=304.2 [M+H+]).

Workup

  1. customto give a light yellow solution
  2. customThe reaction mixture was evaporated to dryness
  3. dissolutionThe crude material was dissolved in 100 ml dichloromethane
  4. extractionextracted with 50 ml
  5. washThe aqueous layers were washed with 40 ml dichloromethane
  6. dry with materialThe organic layer was dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3a7ed0222c1f48bca3b66ccadb16125d
Source dataset
uspto-grants-2014_05
Patent number
US08729061B2

Reaction notes

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