t-Butyl (S)-5-benzyloxy-3-oxononanoate → t-Butyl (3S,5S)-5-benzyloxy-3-hydroxynonanoate

HRID 2289381Notes

Reaction equation

HRID 2289381 reaction equation
[CH2:1]([O:8][C@@H:9]([CH2:21][CH2:22][CH2:23][CH3:24])[CH2:10][C:11](=[O:20])[CH2:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CO>[CH2:1]([O:8][C@@H:9]([CH2:21][CH2:22][CH2:23][CH3:24])[CH2:10][C@H:11]([OH:20])[CH2:12][C:13]([O:15][C:16]([CH3:17])([CH3:18])[CH3:19])=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 54314055t-Butyl (S)-5-benzyloxy-3-oxononanoate

Product 1

HCID 57214808t-Butyl (3S,5S)-5-benzyloxy-3-hydroxynonanoateYield 73.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a 500 ml autoclave were charged 95 ml of dried methanol, 22.0 g of the compound obtained in Step 2, and 0.634 g of (S)-iodo-π-p-cymene[2,2'-bis(di-p-tolylphosphino)-1,1'-binaphthyl]ruthenium iodide in a nitrogen stream, and the mixture was allowed to react at room temperature under a hydrogen pressure of 75 to 80 kg/cm2 for 18 hours. The solvent was removed by distillation under reduced pressure to obtain 22.3 g of a crude product. Purification by silica gel column chromatography gave 16.3 g (73.4%) of the titled compound.

Workup

  1. customto react at room temperature under a hydrogen pressure of 75 to 80 kg/cm2 for 18 hours
  2. customThe solvent was removed by distillation under reduced pressure
  3. customto obtain 22.3 g of a crude product
  4. customPurification by silica gel column chromatography

Sources & evidence

ORD record
ord-6e70f0fa855e4fa4967be9d7a3c0da0b
Source dataset
uspto-grants-2000_07
Patent number
US06093345

Reaction notes

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