(E)-2-[2-(tert-Butoxy)-2-oxoethyl]-5-phenyl-2-pentenoic acid → (R)-2-[2-(tert-butoxy)-2-oxoethyl]-5-phenylpentanoic acid

HRID 1281249Notes

Reaction equation

HRID 1281249 reaction equation
[C:1]([O:5][C:6](=[O:21])[CH2:7]/[C:8](=[CH: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>[C:1]([O:5][C:6](=[O:21])[CH2:7][C@@H:8]([CH2:12][CH2:13][CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[C:9]([OH:11])=[O:10])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 1

HCID 9835650(E)-2-[2-(tert-Butoxy)-2-oxoethyl]-5-phenyl-2-pentenoic acid

Product 1

HCID 10803584(R)-2-[2-(tert-butoxy)-2-oxoethyl]-5-phenylpentanoic acidYield 99.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of (E)-2-[2-(tert-butoxy)-2-oxoethyl]-5-phenyl-2-pentenoic acid (5.8g, 20 mmol) and 1,1′-bis[(2S,4S)-2,4-diethylphosphetano]ferrocene-(1,5-cyclooctadiene)-rhodium (I) tetrafluoroborate (7.4 mg, 10 μmol) in methanol (10 ml) was stirred at 20-25° C. for 24 hours, under hydrogen (4 atmospheres, 60 p.s.i.). The mixture was then concentrated in vacuo to leave the title compound as a yellow oil (5.8 g, 98% conversion, enantiomeric excess=97%, 95% pure by NMR).

Workup

  1. concentrationThe mixture was then concentrated in vacuo

Sources & evidence

ORD record
ord-521eaf68ddae4bf29b7ec9761f068b67
Source dataset
uspto-grants-2002_09
Patent number
US06452041B1

Reaction notes

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