Methyl iodide → 1-benzyl-2-(methoxycarbonyl)-5-(methylthio)-3,4-dihydro-2H-pyrrolium iodide

HRID 1246700Notes

Reaction equation

HRID 1246700 reaction equation
[CH2:1]([N:8]1[C:12](=[S:13])[CH2:11][CH2:10][CH:9]1[C:14]([O:16][CH3:17])=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[I:18][CH3:19]>>[I-:18].[CH2:1]([N+:8]1[CH:9]([C:14]([O:16][CH3:17])=[O:15])[CH2:10][CH2:11][C:12]=1[S:13][CH3:19])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 6328Methyl iodideHCID 14759675Methyl 1-benzyl-5-thioxo-2-pyrrolidinecarboxylate

Product 1

HCID 865958731-benzyl-2-(methoxycarbonyl)-5-(methylthio)-3,4-dihydro-2H-pyrrolium iodide

Procedure

Methyl 1-benzyl-5-thioxo-2-pyrrolidinecarboxylate (16.5 g, 66.2 mmol) in iodomethane (70 mL) was stirred overnight at room temperature. The mixture was concentrated under reduced pressure to provide the title compound which was used in the next step without further purification. 1H NMR (CDCl3) δ 2.24 (m, 1H), 3.04 (s, 3H), 3.16 (m, 1H), 3.25 (m, 1H), 3.63 (s, 3H), 4.29 (dd, 1H), 4.72 (d, 1H), 4.89 (dd, 1H), 5.14 (d, 1H), 7.43 (m, 3H), 7.51 (m, 2H).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-7f98bbabb7804e23af4bd5e0ec642d2e
Source dataset
uspto-grants-2006_10
Patent number
US07129235B2

Reaction notes

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