Methyl iodide → HCID 57024949, compound

HRID 1650314Notes

Reaction equation

HRID 1650314 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-503758b6ed1942a6a0cb9d4cf2b1e148
Source dataset
uspto-grants-1990_05
Patent number
US04923857

Reaction notes

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