Methyl iodide → HCID 57024949, compound

HRID 1090544Notes

Reaction equation

HRID 1090544 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 57287692HCID 57287692, compound

Product 1

HCID 57024949HCID 57024949, compound

Reagents, catalysts & solvents 1

HCID 92152Silver(II) oxideCatalyst

Procedure

To a solution of (2S,4S)-1-allyloxycarbonyl-4-hydroxy-2-(2-methyl-3-oxo-1-butenyl)pyrrolidine (4.00 g) in iodomethane (20 ml) was added silver oxide (20 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 (50 ml) eluting with a mixture of n-hexane and ethyl acetate (6:4 V/V) to give (2S,4S)-1-allyloxycarbonyl-4-methoxy-2-(2-methyl-3-oxo-1-butenyl)pyrrolidine (2.31 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 (50 ml)
  4. washeluting with a mixture of n-hexane and ethyl acetate (6:4 V/V)

Sources & evidence

ORD record
ord-2f48690bd66d4b46b58825cb1b956133
Source dataset
uspto-grants-1992_01
Patent number
US05081237

Reaction notes

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