8-Hydroxy-6-oxo-octanoic acid methyl ester → (R)-6,8-dihydroxyoctanoic acid methyl ester

HRID 1063473Notes

Reaction equation

HRID 1063473 reaction equation
[CH3:1][O:2][C:3](=[O:13])[CH2:4][CH2:5][CH2:6][CH2:7][C:8](=[O:12])[CH2:9][CH2:10][OH:11]>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.O=O>[CH3:1][O:2][C:3](=[O:13])[CH2:4][CH2:5][CH2:6][CH2:7][C@@H:8]([OH:12])[CH2:9][CH2:10][OH:11]

Participants

4

Reactant 1

HCID 120390238-Hydroxy-6-oxo-octanoic acid methyl ester

Product 1

HCID 10442514(R)-6,8-dihydroxyoctanoic acid methyl esterYield 85%

Reagents, catalysts & solvents 2

HCID 634876Binap, (A+-)-CatalystHCID 977OxygenSolvent

Procedure

A 100 ml autoclave was charged under argon with 3.8 g (20 mmol) of 8-hydroxy-6-oxo-octanoic acid methyl ester, with the Ru-(R)-BINAP catalyst solution prepared under Example 1, and with 20 ml of oxygen-free methanol. The hydrogenation was carried out for 20 hours at 60° C., at a constant pressure of 40 bar pure H2 and with intensive stirring. When the reaction was complete, the solvent was distilled off using a rotary evaporator. Purification of the residue by column chromatography (silica gel, ethyl acetate/n-hexane) yielded 3.2 g (85%) of (R)-6,8-dihydroxyoctanoic acid methyl ester having an enantiomeric excess of 96% (chiral GC).

Workup

  1. customprepared under Example 1
  2. distillationthe solvent was distilled off
  3. customa rotary evaporator
  4. customPurification of the residue by column chromatography (silica gel, ethyl acetate/n-hexane)

Sources & evidence

ORD record
ord-fd9131747d5c4e46a7b1d0e8c0e009d6
Source dataset
uspto-grants-2005_11
Patent number
US06965029B2

Reaction notes

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