Methanol → HCID 19915060, compound

HRID 1090335Notes

Reaction equation

HRID 1090335 reaction equation
[CH2:1]([N:8]1[CH:11]([C:12]([C:14]([OH:16])=[O:15])=[CH2:13])[CH:10]([CH:17]([OH:19])[CH3:18])[C:9]1=[O:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:21]O>[Pd]>[CH2:1]([N:8]1[CH:11]([CH:12]([C:14]([O:16][CH3:21])=[O:15])[CH3:13])[CH:10]([CH:17]([OH:19])[CH3:18])[C:9]1=[O:20])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 19915055HCID 19915055, compound

Product 1

HCID 19915060HCID 19915060, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

To a solution of 38 mg (0.14 mmol) of 1-benzyl-4-(1-carboxyethenyl)-3-(1-hydroxyethyl)-2-azetidinone dissolved in 1 ml of methanol, 5 mg of 5% palladium charcoal was added and the mixture was stirred under hydrogen atmosphere for a night. The reaction solution was filtered with selite, the filtrate was added with an ethereal solution of diazomethane and the resultant was concentrated. The concentrate was purified with 2 g of silica-gel column (benzene:ethyl acetate 1:1) to give 30 mg of 1-benzyl-4-(1-methoxycarbonylethyl)-3-(1-hydroxyethyl)-2-azetidinone (yield: 78%).

Workup

  1. filtrationThe reaction solution was filtered with selite
  2. additionthe filtrate was added with an ethereal solution of diazomethane
  3. concentrationthe resultant was concentrated
  4. customThe concentrate was purified with 2 g of silica-gel column (benzene:ethyl acetate 1:1)

Sources & evidence

ORD record
ord-01399a81faf84493ab4e0888324de35e
Source dataset
uspto-grants-1992_01
Patent number
US05081238

Reaction notes

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