Ethanethiol → (2S)-2-[(1R,2S)-2-benzyloxycarbonyl-1-ethylsulfanyl-propyl]-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 1582737Notes

Reaction equation

HRID 1582737 reaction equation
CC([O-])(C)C.[K+].[CH3:7][CH2:8][SH:9].[C:10]([O:14][C:15]([N:17]1[CH2:21][CH2:20][CH2:19][C@H:18]1[CH:22]=[C:23]([C:25]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26])[CH3:24])=[O:16])([CH3:13])([CH3:12])[CH3:11]>C1COCC1>[C:10]([O:14][C:15]([N:17]1[CH2:21][CH2:20][CH2:19][C@H:18]1[C@H:22]([S:9][CH2:8][CH3:7])[C@H:23]([C:25]([O:27][CH2:28][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)=[O:26])[CH3:24])=[O:16])([CH3:11])([CH3:12])[CH3:13]

Participants

5

Reactant 3

HCID 6343EthanethiolHCID 23665647Potassium tert-butoxideHCID 69343930(S)-2-(2-Benzyloxycarbonyl-propenyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 69551098(2S)-2-[(1R,2S)-2-benzyloxycarbonyl-1-ethylsulfanyl-propyl]-pyrrolidine-1-carboxylic acid tert-butyl esterYield 83.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred suspension of t-BuOK (609 mg, 5.43 mmol) in THF (90 ml) was added EtSH (8.04 ml, 0.11 mol). After stirring for 30 min at room temperature, a solution of (2S)-2-(2-benzyloxycarbonyl-propenyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (3.75 g, 10.8 mmol) in THF (75 ml) was added to the mixture. After 2.5 h, the mixture was quenched with saturated NH4Cl aqueous solution, and then concentrated in vacuo. The residue was diluted with EtOAc (400 ml), and washed with saturated NH4Cl aqueous solution (150 ml), saturated NaHCO3 aqueous solution (150 ml) and H2O (150 ml). The organic layer was dried over anhydrous Na2SO4, and then concentrated in vacuo. The residue was purified by column chromatography on silica gel (hexane/EtOAc=12/1 to 8/1) to give (2S)-2-[(1R,2S)-2-benzyloxycarbonyl-1-ethylsulfanyl-propyl]-pyrrolidine-1-carboxylic acid tert-butyl ester (3.66 g, 83%).

Workup

  1. waitAfter 2.5 h
  2. customthe mixture was quenched with saturated NH4Cl aqueous solution
  3. concentrationconcentrated in vacuo
  4. additionThe residue was diluted with EtOAc (400 ml)
  5. washwashed with saturated NH4Cl aqueous solution (150 ml), saturated NaHCO3 aqueous solution (150 ml) and H2O (150 ml)
  6. dry with materialThe organic layer was dried over anhydrous Na2SO4
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by column chromatography on silica gel (hexane/EtOAc=12/1 to 8/1)

Sources & evidence

ORD record
ord-56c16a886e8147d3ba501e3d0dbd18a4
Source dataset
uspto-grants-2004_05
Patent number
US06737409B2

Reaction notes

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