Citric Acid → tert-Butyl (3S)-3-sulfanylpyrrolidine-1-carboxylate

HRID 241664Notes

Reaction equation

HRID 241664 reaction equation
C([S:4][C@H:5]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6]1)(=O)C.C(=O)([O-])[O-].[K+].[K+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CO>[SH:4][C@H:5]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6]1

Participants

5

Reactant 3

HCID 311Citric AcidHCID 11430Potassium CarbonateHCID 59560788Tert-butyl (S)-3-(acetylthio)pyrrolidine-1-carboxylate

Product 1

HCID 59032356tert-Butyl (3S)-3-sulfanylpyrrolidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of (S)-tert-butyl 3-(acetylthio)pyrrolidine-1-carboxylate (STEP B, 1.82 g, 7.42 mmol) in methanol (15 mL) was added potassium carbonate (2.05 g, 14.8 mmol). The mixture was stirred at 50° C. for 2 h. Then the mixture was cooled to room temperature, acidified by addition of 20% citric acid aqueous solution and concentrated in vacuo to remove methanol. The residue was diluted with ethyl acetate to separate. The organic layer was dried over sodium sulfate and concentrated in vacuo. The crude product was used for the next step without purification.

Workup

  1. temperatureThen the mixture was cooled to room temperature
  2. concentrationconcentrated in vacuo
  3. customto remove methanol
  4. additionThe residue was diluted with ethyl acetate
  5. customto separate
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe crude product was used for the next step without purification

Sources & evidence

ORD record
ord-300c6dcf8bec449d85272d01e9ce0b5c
Source dataset
uspto-grants-2014_02
Patent number
US08653063B2

Reaction notes

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