Hydrochloric Acid → tert-Butyl 3-sulfanylpyrrolidine-1-carboxylate

HRID 1280745Notes

Reaction equation

HRID 1280745 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([S:13]C(=O)C)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C[O-].[Na+].Cl>CO>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([SH:13])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 54776232tert-Butyl 3-(acetylthio)pyrrolidine-1-carboxylate

Product 1

HCID 13324658tert-Butyl 3-sulfanylpyrrolidine-1-carboxylateYield 116.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Procedure

To a 0° C. solution of (RS)-3-acetylsulfanyl-pyrrolidine-1-carboxylic acid tert-butyl ester (1.4 g, 5.07 mmol) in MeOH (15 ml) was added dropwise a suspension of sodium methoxide (0.61 g, 11.3 mmol) in MeOH. After 6 hours stirring at room temperature, the reaction mixture was neutralized with 1N HCl and MeOH was partially evaporated. H2O and ethylacetate were added. The aqueous phase was extracted with ethylacetate, the combined organic phases were washed with brine, dried over Na2SO4, filtered and concentrated to provide (RS)-3-mercapto-pyrrolidine-1-carboxylic acid tert-butyl ester (1.2 g, 100%) as a colorless oil, MS: m/e 130.1 (M-OtBu).

Workup

  1. customwas partially evaporated
  2. additionH2O and ethylacetate were added
  3. extractionThe aqueous phase was extracted with ethylacetate
  4. washthe combined organic phases were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-5de6308f5bba43c58c0b380742c1fe91
Source dataset
uspto-grants-2002_09
Patent number
US06451819B2

Reaction notes

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