Methyl iodide → HCID 57315470, compound

HRID 1090499Notes

Reaction equation

HRID 1090499 reaction equation
[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@H:10]([OH:12])[CH2:9][C@H:8]1[CH:13]=[C:14]([CH3:18])[C:15](=[O:17])[CH3:16])=[O:6])[CH:2]=[CH2:3].I[CH3:20]>[Ag]=O>[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@H:10]([O:12][CH3:20])[CH2:9][C@H:8]1[CH:13]=[C:14]([CH3:18])[C:15](=[O:17])[CH3:16])=[O:6])[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 57026776HCID 57026776, compound

Product 1

HCID 57315470HCID 57315470, compound

Reagents, catalysts & solvents 1

HCID 92152Silver(II) oxideCatalyst

Procedure

To a solution of (2S,4R)-1-allyloxycarbonyl-4-hydroxy-2-(2-methyl-3-oxo-1-butenyl)pyrrolidine (3.0 g) in iodomethane (15 ml) was added silver oxide (10 g), and the mixture was allowed to stand at ambient temperature for 2 days. The resulting precipitate was removed by filtration and the filtrate was evaporated in vacuo. The residue was chromatographed on silica gel (60 ml) eluting with a mixture of n-hexane and ethyl acetate (6:4 V/V) to give (2S,4R)-1-allyloxycarbonyl-4-methoxy-2-(2-methyl-3-oxo-1-butenyl)pyrrolidine (3.23 g).

Workup

  1. customThe resulting precipitate was removed by filtration
  2. customthe filtrate was evaporated in vacuo
  3. customThe residue was chromatographed on silica gel (60 ml)
  4. washeluting with a mixture of n-hexane and ethyl acetate (6:4 V/V)

Sources & evidence

ORD record
ord-5a7270a49e21448dbaca5fb522435913
Source dataset
uspto-grants-1992_01
Patent number
US05081237

Reaction notes

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