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

HRID 481236Notes

Reaction equation

HRID 481236 reaction equation
[S:1]=[C:2]1[NH:6][C@H:5]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:4][CH2:3]1.[CH3:14]I>C1COCC1>[CH3:14][S:1][C:2]1[CH2:3][CH2:4][C@@H:5]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[N:6]=1

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 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of thiolactam 1b (10.50 g, 52.2 mmol) in 200 mL THF at rt, was added MeI (13.0 mL, 208.7 mmol). The mixture was stirred for 3.5 h, then concentrated. The residue was partitioned between CH2Cl2 and sat. NaHCO3 and the aqueous phase was extracted with CH2Cl2 (3×). The combined organic extract was dried (Na2SO4) and concentrated to afford 10.17 g (91%) of the title compound, 1c, as a brown oil. 1H NMR (300 MHz, CDCl3) δ4.60 (dd, J=6.2, 7.3, 1H), 2.83-2.58 (m, 2H), 2.49 (s, 3H), 2.37-2.22 (m, 1H), 2.17-2.03 (m, 1H), 1.48 (s, 9H).

Workup

  1. concentrationconcentrated
  2. customThe residue was partitioned between CH2Cl2 and sat. NaHCO3
  3. extractionthe aqueous phase was extracted with CH2Cl2 (3×)
  4. extractionThe combined organic extract
  5. dry with materialwas dried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-517d3c7800934dac9b874af78c5cd01d
Source dataset
uspto-grants-2003_11
Patent number
US06653295B2

Reaction notes

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