Methyl (S)-2-methyl-3-phenylpropionate → (S)-2-methyl-3-phenylpropan-1-ol

HRID 2066005Notes

Reaction equation

HRID 2066005 reaction equation
[CH3:1][C@@H:2]([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:3](OC)=[O:4].[H][H]>O1CCCC1>[CH3:1][C@@H:2]([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH2:3][OH:4]

Participants

4

Reactant 2

HCID 11286798Methyl (S)-2-methyl-3-phenylpropionateHCID 178418361HCID 178418361, compound

Product 1

HCID 11804940(S)-2-methyl-3-phenylpropan-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl (S)-2-methyl-3-phenylpropionate (5 mmol, 78.4% ee), a ruthenium complex 1 (0.01 mmol), and tetrahydrofuran (2 mL) were charged into a 100-mL autoclave equipped with a stirrer. Then, the mixture was subjected to hydrogenation at a hydrogen pressure of 5 MPa at 80° C. for 16 hours. The reaction liquid was analyzed by gas chromatography. As a result, (S)-2-methyl-3-phenylpropanol was obtained at a conversion rate of 99.0% and a selectivity of 98.6%. The obtained alcohol had an optical purity of 77.9% ee.

Workup

  1. customequipped with a stirrer
  2. customThe reaction liquid

Sources & evidence

ORD record
ord-1684e154d5224ae196d8585420fa6367
Source dataset
uspto-grants-2012_10
Patent number
US08288575B2

Reaction notes

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