HCID 86752957, compound → HCID 14988922, compound

HRID 481327Notes

Reaction equation

HRID 481327 reaction equation
[CH:1]1([NH:7][C:8]([O:10][CH:11]2[CH2:18][CH2:17][C:14]3([O:16][CH2:15]3)[CH:13]([C:19]3([CH3:30])[CH:21]([CH2:22][CH:23]=[CH:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])[O:20]3)[CH:12]2[O:31][CH3:32])=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>C(OCC)(=O)C.[Pt]=O>[CH:1]1([NH:7][C:8]([O:10][CH:11]2[CH2:18][CH2:17][C:14]3([O:16][CH2:15]3)[CH:13]([C:19]3([CH3:30])[CH:21]([CH2:22][CH2:23][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])[O:20]3)[CH:12]2[O:31][CH3:32])=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 1

HCID 86752957HCID 86752957, compound

Product 1

HCID 14988922HCID 14988922, compound

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 6-cyclohexylcarbamoyloxy-4-[3-(3-ethoxycarbonyl-2-propenyl)-2-methyloxiranyl]-5-methoxy-1-oxaspiro[2,5]octane (46 mg) in ethyl acetate (30 ml) was hydrogenated under hydrogen (1 atm) in the presence of platinum oxide (5 mg) for 2 hours. The catalyst was removed by filtration and the filtrate was concentrated in vacuo. The residue was purified by column chromatography on silica gel eluted with a mixture of diethyl ether and n-hexane (1:1) to give 6-cyclohexylcarbamoyloxy-4-[3-(3-ethoxycarbonylpropyl)-2-methyloxiranyl]-5-methoxy-1-oxaspiro[2,5]octane as an oil.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was purified by column chromatography on silica gel
  4. washeluted with a mixture of diethyl ether and n-hexane (1:1)

Sources & evidence

ORD record
ord-6beef36b1d3641f2939f2073ad93159a
Source dataset
uspto-grants-1998_08
Patent number
US05789405

Reaction notes

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