3-Oxooctanoic acid t-butyl ester → (R)-3-hydroxyoctanoic acid t-butyl ester

HRID 1695164Notes

Reaction equation

HRID 1695164 reaction equation
[C:1]([O:5][C:6](=[O:15])[CH2:7][C:8](=[O:14])[CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])([CH3:4])([CH3:3])[CH3:2]>CO.C1C=CC(P(C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Ru]Cl>[C:1]([O:5][C:6](=[O:15])[CH2:7][C@H:8]([OH:14])[CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])([CH3:3])([CH3:2])[CH3:4]

Participants

4

Reactant 1

HCID 124253683-Oxooctanoic acid t-butyl ester

Product 1

HCID 86645801(R)-3-hydroxyoctanoic acid t-butyl esterYield 90.5%

Reagents, catalysts & solvents 2

HCID 11136527(R)-[2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl dichlororutheniumCatalystHCID 887MethanolSolvent

Procedure

The 3-oxooctanoic acid t-butyl ester (4.50 g, 21.0 mmol) obtained in Production Example A-1 and dichloro [(R)-(+)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl]ruthenium (II) (hereunder abbreviated as (R)-BINAP-RuCl2) (40 mg, 50.3 μmol) were dissolved in methanol (10 ml) freeze-degassed with liquid nitrogen. The obtained methanol solution was stirred for 42 hours using an autoclave (SUS-316; Taiatsu) at room temperature under 60 atm of hydrogen. The reaction solution was then condensed, and purified using column chromatography (silica gel: 150 g, n-hexane/ethyl acetate=10/1) to produce the target compound (4.11 g, 89%).

Workup

  1. customfreeze-degassed with liquid nitrogen
  2. customat room temperature
  3. customcondensed
  4. custompurified

Sources & evidence

ORD record
ord-107f28a3f6fa46b2bec557dfdef6fcf5
Source dataset
uspto-grants-2012_04
Patent number
US08163713B2

Reaction notes

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