HCID 66771697, compound → HCID 86648102, compound

HRID 1875288Notes

Reaction equation

HRID 1875288 reaction equation
[C:1]([O:7][C:8]1([CH3:17])[CH2:13][CH2:12][CH:11]([CH:14]([CH3:16])[CH3:15])[CH2:10][CH2:9]1)(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4]>CO>[OH:4][C@@H:3]([CH3:5])[CH2:2][C:1]([O:7][C:8]1([CH3:17])[CH2:9][CH2:10][CH:11]([CH:14]([CH3:15])[CH3:16])[CH2:12][CH2:13]1)=[O:6]

Participants

3

Reactant 1

HCID 66771697HCID 66771697, compound

Product 1

HCID 86648102HCID 86648102, compoundYield 98.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

144.2 g (0.60 mol) of 1-menthyl acetoacetate, 98.8 mg (12.0 μmol) of a catalyst [{RuCl((S)-SEGPHOS)}2(μ-Cl)3][NH2Me2] and 75 ml of methanol were put into a 500 ml capacity autoclave and allowed to undergo the reaction at 70° C. for 5.5 hours under a hydrogen pressure of 4 MPa. The thus obtained reaction solution was subjected to evaporation of the solvent and then distilled under a reduced pressure (121° C./170 Pa) to obtain 143.1 g (yield 98.4%) of the (3S)-1-menthyl 3-hydroxybutyrate of interest as a colorless oily substance.

Workup

  1. customthe reaction at 70° C. for 5.5 hours under a hydrogen pressure of 4 MPa
  2. customThe thus obtained reaction solution
  3. customwas subjected to evaporation of the solvent
  4. distillationdistilled under a reduced pressure (121° C./170 Pa)

Sources & evidence

ORD record
ord-25b993a3f97a4a8a8b2c47912e86d063
Source dataset
uspto-grants-2012_11
Patent number
US08309062B2

Reaction notes

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