(R)-2-[2-(tert-butoxy)-2-oxoethyl]-5-phenylpentanoic acid → (2R)-2-[2-(tert-butoxy)-2-oxoethyl]-5-cyclohexylpentanoic acid

HRID 2182965Notes

Reaction equation

HRID 2182965 reaction equation
[C:1]([O:5][C:6](=[O:21])[CH2:7][C@@H:8]([CH2:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:9]([OH:11])=[O:10])([CH3:4])([CH3:3])[CH3:2]>CO.[Rh]>[C:1]([O:5][C:6](=[O:21])[CH2:7][C@@H:8]([CH2:12][CH2:13][CH2:14][CH:15]1[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]1)[C:9]([OH:11])=[O:10])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 10803584(R)-2-[2-(tert-butoxy)-2-oxoethyl]-5-phenylpentanoic acid

Product 1

HCID 9835906(2R)-2-[2-(tert-butoxy)-2-oxoethyl]-5-cyclohexylpentanoic acidYield 89.4%

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 887MethanolSolvent

Procedure

A solution of (R)-2-[2-(tert-butoxy)-2-oxoethyl]-5-phenylpentanoic acid (2.2 g, 7.5 mmol) and 5%Rh/C (0.22 g) in methanol (220 ml) was stirred at room temperature, under hydrogen (150 p.s.i.) for 24 hours and then filtered through celite. The filtrate was concentrated in vacuo to leave the title compound as an oil (2.0 g).

Workup

  1. filtrationfiltered through celite
  2. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-01d74e3edaa0422ca7cdb2d2d2baa0bf
Source dataset
uspto-grants-2005_05
Patent number
US06897306B2

Reaction notes

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