Ethanethiol → Ethyl 3-(1-Boc-2-pyrrolidinyl)acrylate

HRID 1582727Notes

Reaction equation

HRID 1582727 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH:13]=[CH:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[O:7])([CH3:4])([CH3:3])[CH3:2].CCS.[H-].[Na+]>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[CH:13]=[CH:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6343EthanethiolHCID 24758Sodium hydrideHCID 57264746HCID 57264746, compound

Product 1

HCID 53933727Ethyl 3-(1-Boc-2-pyrrolidinyl)acrylateYield 132.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of (S)-2-(2-ethoxycarbonyl-vinyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (103 mg, 0.382 mmol) in THF (2 ml) was added EtSH (85 μl, 1.15 mmol) and NaH (60% in paraffin liquid: 46 mg, 1.15 mmol) at 0° C. The mixture was allowed to warm to room temperature and stirred for 7 hr. The mixture was quenched with 1N HCl, extracted with AcOEt, washed with saturated aqueous NaCl, dried (MgSO4), and concentrated in vacuo to give 2-(2-ethoxycarbonyl-vinyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (136 mg) as a crude oil, which was used without further purification in the next step.

Workup

  1. customThe mixture was quenched with 1N HCl
  2. extractionextracted with AcOEt
  3. washwashed with saturated aqueous NaCl
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-64ff5eb72b734d01b222758d2c56088f
Source dataset
uspto-grants-2004_05
Patent number
US06737409B2

Reaction notes

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