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

HRID 10953Notes

Reaction equation

HRID 10953 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.[CH2:14]1COCC1>>[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

3

Reactant 2

HCID 8028TetrahydrofuranHCID 14416882tert-Butyl (S)-5-thioxo-2-pyrrolidinecarboxylate

Product 1

HCID 53965507tert-Butyl (S)-5-(methylsulfanyl)-3,4-dihydro-2H-pyrrole-2-carboxylateYield 91%

Procedure

To a solution of thiolactam 1b (10.50 g, 52.2 mmol) in 200 mL THF at rt, was added Mel (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) δ 4.60 (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-9b0a2c977b72425c90a00e57ab227d60
Source dataset
uspto-grants-2006_08
Patent number
US07094783B2

Reaction notes

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