HCID 57238212, compound → HCID 53809183, compound

HRID 1740544Notes

Reaction equation

HRID 1740544 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[CH:5]=[CH:6][CH2:7][C@@H:8]([CH3:16])[CH2:9][CH2:10][CH:11]1[C:13]([CH3:15])([CH3:14])[O:12]1)[CH3:2]>CCOC(C)=O.[Pd]>[CH2:1]([O:3][C:4](=[O:17])[CH2:5][CH2:6][CH2:7][C@@H:8]([CH3:16])[CH2:9][CH2:10][CH:11]1[C:13]([CH3:15])([CH3:14])[O:12]1)[CH3:2]

Participants

4

Reactant 1

HCID 57238212HCID 57238212, compound

Product 1

HCID 53809183HCID 53809183, compoundYield 82.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

9.59 g of (5S)-7-((RS)-3,3-dimethyl-oxiranyl)-5-methyl-hept-2-enoic acid ethyl ester was hydrogenated at RT in 57 ml of AcOEt over 960 mg of Pd/C (5%) for 6 h. At that time, GC analysis indicated the complete disappearance of starting material. Filtration and flash chromatography (SiO2, hexane/AcOEt=9/1) afforded 7.98 g of (5R)-7-((RS)-3,3-dimethyl-oxiranyl)-5-methyl-heptanoic acid ethyl ester (roughly 1/1 epimeric mixture) as colorless oil.

Workup

  1. filtrationFiltration and flash chromatography (SiO2, hexane/AcOEt=9/1)

Sources & evidence

ORD record
ord-dc3fc33bc4334418adb130115ce387bd
Source dataset
uspto-grants-1999_10
Patent number
US05969190

Reaction notes

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