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

HRID 2239563Notes

Reaction equation

HRID 2239563 reaction equation
C([S:4][CH: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[S-].[Na+].Cl>CO>[SH:4][CH: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 313Hydrochloric AcidHCID 4378561Sodium methanethiolateHCID 54776232tert-Butyl 3-(acetylthio)pyrrolidine-1-carboxylate

Product 1

HCID 13324658tert-Butyl 3-sulfanylpyrrolidine-1-carboxylateYield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

tert-Butyl 3-(acetylthio)pyrrolidine-1-carboxylate (200 mg, 0.81 mmol) was dissolved in MeOH (10mL) and sodium methanethiolate (57 mg, 0.81 mmol) was added. The reaction mixture was stirred at rt for 30 mins. HCl (1M solution) was added and the aqueous layer extracted with DCM. The organic layer was washed with brine, dried (Na2SO4), filtered and evaporated affording the title compound (0.163 g, 98.4%). 1H NMR (500 MHz, CDCl3): δ 1.44 (s, 9H), 1.68 (d, 1H), 1.75-1.84 (m, 1H), 2.22-2.28 (m, 1H), 3.13-3.23 (m, 1H), 3.30-3.40 (m, 2H), 3.47-3.57 (m, 1H), 3.67-3.74 (m, 1H).

Workup

  1. extractionthe aqueous layer extracted with DCM
  2. washThe organic layer was washed with brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-41b14c9d5fa94d7999adc86c6e9f609b
Source dataset
uspto-grants-2010_05
Patent number
US07723333B2

Reaction notes

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