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Water → (2R,4S)-4-Acetoxy-1-(toluene-4-sulfonyl)-pyrrolidine-2-carboxylic Acid Ethyl Ester

HRID 906217
Notes
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Reaction equation

HRID 906217 reaction equation
[CH2:1]([O:3][C:4]([C@H:6]1[CH2:10][C@@H:9]([O:11]S(C2C=CC(C)=CC=2)(=O)=O)[CH2:8][N:7]1[S:22]([C:25]1[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=1)(=[O:24])=[O:23])=[O:5])[CH3:2].[C:32]([O-])(=[O:34])[CH3:33].[K+].O>CN(C=O)C>[CH2:1]([O:3][C:4]([C@H:6]1[CH2:10][C@H:9]([O:11][C:32](=[O:34])[CH3:33])[CH2:8][N:7]1[S:22]([C:25]1[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=1)(=[O:23])=[O:24])=[O:5])[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 962WaterHCID 517044Potassium AcetateHCID 14541195(2R,4R)-1-(Toluene-4-sulfonyl)-4-(toluene-4-sulfonyloxy)-pyrrolidine-2-carboxylic Acid Ethyl Ester

Product 1

HCID 15629284(2R,4S)-4-Acetoxy-1-(toluene-4-sulfonyl)-pyrrolidine-2-carboxylic Acid Ethyl Ester

Reagents, catalysts & solvents 1

HCID 6228Dimethylformamide
Solvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of 1-(toluene-4-sulfonyl)-4-(toluene-4-sulfonyloxy)-pyrrolidine-2-carboxylic acid ethyl ester (2) (1 g, 2.14 mmol) in dry DMF (25 mL) is added potassium acetate (0.314 g, 3.21 mmol) in one portion. The reaction mixture is then heated at 60° C. for 4 h. Water (50 mL) is added to the reaction mixture and extracted with ethyl acetate (2×75 mL), combined organic layer are washed with water (2×50 mL), dried (Na2SO4), filtered, and concentrated under reduced pressure to give the crude compound. Crude compound is purified by column chromatography over silica gel (100-200 mesh) using 15% ethyl acetate-hexane as eluent to give compound (3).

Workup

  1. extractionextracted with ethyl acetate (2×75 mL)
  2. washare washed with water (2×50 mL)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto give the crude compound
  7. customCrude compound is purified by column chromatography over silica gel (100-200 mesh)

Sources & evidence

ORD record
ord-9e2f7a1d3fd6492999db3178fcc2497d
Source dataset
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08012983B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes