(E)-2-[2-(tert-butoxy)-2-oxoethyl]-5-(2-methyl-1,1'-biphenyl-4-yl)-2-pentenoic acid → (R)-2-[2-(tert-butoxy)-2-oxoethyl]-5-(2-methyl-1,1'-biphenyl-4-yl)-pentanoic acid

HRID 353397Notes

Reaction equation

HRID 353397 reaction equation
[C:1]([O:5][C:6](=[O:28])[CH2:7]/[C:8](=[CH:12]\[CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[C:17]([CH3:27])[CH:16]=1)/[C:9]([OH:11])=[O:10])([CH3:4])([CH3:3])[CH3:2]>CO>[C:1]([O:5][C:6](=[O:28])[CH2:7][C@@H:8]([CH2:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)=[C:17]([CH3:27])[CH:16]=1)[C:9]([OH:11])=[O:10])([CH3:3])([CH3:4])[CH3:2]

Participants

3

Reactant 1

HCID 22708851(E)-2-[2-(tert-butoxy)-2-oxoethyl]-5-(2-methyl-1,1'-biphenyl-4-yl)-2-pentenoic acid

Product 1

HCID 11825126(R)-2-[2-(tert-butoxy)-2-oxoethyl]-5-(2-methyl-1,1'-biphenyl-4-yl)-pentanoic acidYield 99.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of (E)-2-[2-(tert-butoxy)-2-oxoethyl]-5-(2-methyl-1,1′-biphenyl-4-yl)-2-pentenoic acid (3.8 g, 10 mmol) and 1,1′-bis[(2S,4S)-2,4-diethylphosphetano]ferrocene-(1,5-cyclooctadiene)-rhodium (I) tetrafluoroborate (7.8 mg, 10 μmol) in methanol (10 ml) was stirred at 20-25° C. for 24 hours, under hydrogen (60 p.s.i.). The mixture was then concentrated in vacuo to leave the title compound as a yellow oil (3.8 g, 98% conversion, enantiomeric excess=95%, 95% pure by NMR).

Workup

  1. concentrationThe mixture was then concentrated in vacuo

Sources & evidence

ORD record
ord-79bb505a5faa498b96302f26b3c10f3a
Source dataset
uspto-grants-2004_06
Patent number
US06750363B2

Reaction notes

Loading…