HCID 54345618, compound → HCID 11128482, compound

HRID 636012Notes

Reaction equation

HRID 636012 reaction equation
[CH2:1]([C@H:8]([C@H:13]([OH:17])[CH2:14][CH2:15][CH3:16])[C:9]([O:11][CH3:12])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CO.[Rh]>[CH:2]1([CH2:1][C@H:8]([C@H:13]([OH:17])[CH2:14][CH2:15][CH3:16])[C:9]([O:11][CH3:12])=[O:10])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

4

Reactant 1

HCID 54345618HCID 54345618, compound

Product 1

HCID 11128482HCID 11128482, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 887MethanolSolvent

Procedure

Methyl (2R,3R)-2-benzyl-3-hydroxyhexanoate (3.35 g, 14.2 mmol) is dissolved in 35 mL of MeOH. Under an argon atmosphere 1.00 g of 5% rhodium on carbon is added. The reaction vessel is evacuated and refilled with hydrogen several times and then pressurized with hydrogen to 65 psi. After 8 h the reaction vessel is evacuated and refilled with nitrogen. The solution is filtered and the filtrate concentrated in vacuo giving methyl (2R,3R)-2-cyclohexylmethyl-3-hydroxyhexanoate as an oil (3.44 g, 99% yield).

Workup

  1. customThe reaction vessel is evacuated
  2. additionrefilled with hydrogen several times
  3. customAfter 8 h the reaction vessel is evacuated
  4. additionrefilled with nitrogen
  5. filtrationThe solution is filtered
  6. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-912f60c53341440e9bdd8c56f754973d
Source dataset
uspto-grants-2001_02
Patent number
US06191150B1

Reaction notes

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