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

HRID 2307485Notes

Reaction equation

HRID 2307485 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].[H][H]>C(O)(=O)C.[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

5

Reactant 2

HCID 10803584(R)-2-[2-(tert-butoxy)-2-oxoethyl]-5-phenylpentanoic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 9835906(2R)-2-[2-(tert-butoxy)-2-oxoethyl]-5-cyclohexylpentanoic acidYield 73.8%

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of (2R)-2-[2-(tert-butoxy)-2-oxoethyl]-5-phenylpentanoic acid (Syn. Lett.; 1998; 637-639) (10.00 g, 34.2 mmol) in acetic acid (120 m)) was treated with 5% Rhodium on alumina catalyst, pressurised to 60 psi with hydrogen in a seated vessel and stirred at room temperature for 17 hours. The mixture was filtered through a pad of Arbocel® and the solvent was removed from the filtrate under reduced pressure. The residue was azeotroped from toluene to afford the title compound (7.53 g).

Workup

  1. filtrationThe mixture was filtered through a pad of Arbocel®
  2. customthe solvent was removed from the filtrate under reduced pressure
  3. customThe residue was azeotroped from toluene

Sources & evidence

ORD record
ord-c86af5f8d76843778281a37c3c103775
Source dataset
uspto-grants-2004_12
Patent number
US06831088B2

Reaction notes

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