Methyl iodide → tert-Butyl (S)-5-(methylsulfanyl)-3,4-dihydro-2H-pyrrole-2-carboxylate

HRID 1737850Notes

Reaction equation

HRID 1737850 reaction equation
[C:1]([O:5][C:6]([C@H:8]1[NH:12][C:11](=[S:13])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:14]I>C1COCC1>[C:1]([O:5][C:6]([C@H:8]1[N:12]=[C:11]([S:13][CH3:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 14416882tert-Butyl (S)-5-thioxo-2-pyrrolidinecarboxylate

Product 1

HCID 53965507tert-Butyl (S)-5-(methylsulfanyl)-3,4-dihydro-2H-pyrrole-2-carboxylateYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)-pyrrolidin-2-thione-5-carboxylic acid t-butyl ester (1.75 g, 8.71 mmol) in 35 mL of dry THF was added MeI (2.2 mL, 34.83 mmol) at rt. The mixture was stirred at rt for 3 h and concentrated under vacuum. CH2Cl2 was added to the resulting oil which was poured into a sat. solution of NaHCO3. This was extracted 3 times with CH2Cl2, dried over MgSO4, and concentrated to provide (S)-2-methylsulfanyl-3,4-dihydro-5H-pyrrole-5-carboxylic acid t-butyl ester (1.63 g, 87%) as a brown oil which was used without further purification 1H NMR (CDCl3) δ 1.46 (s, 9H), 2.09 (m, 1H), 2.28 (m, 1H), 2.48 (s, 3H), 2.56-2.80 (m, 2H), 4.59 (m, 1H). MS calcd for C10H17NO2S+H, 216, found 216.

Workup

  1. concentrationconcentrated under vacuum
  2. additionCH2Cl2 was added to the resulting oil which
  3. additionwas poured into a sat. solution of NaHCO3
  4. extractionThis was extracted 3 times with CH2Cl2
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-23fa2cafdf0b488a985b3da066b37d14
Source dataset
uspto-grants-1999_10
Patent number
US05962487

Reaction notes

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