2-[1-biphenyl-4-yl-meth-(Z)-ylidene]-succinic acid 4-tert-butyl ester 1-methyl ester → 2-Biphenyl-4-ylmethyl-succinic acid 4-tert-butyl ester 1-methyl ester

HRID 70876Notes

Reaction equation

HRID 70876 reaction equation
[CH3:1][O:2][C:3](=[O:26])/[C:4](=[CH:13]\[C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:16][CH:15]=1)/[CH2:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7]>C(OCC)(=O)C.[Pt]>[CH3:1][O:2][C:3](=[O:26])[CH:4]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:16][CH:15]=1)[CH2:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7]

Participants

4

Reactant 1

HCID 684245312-[1-biphenyl-4-yl-meth-(Z)-ylidene]-succinic acid 4-tert-butyl ester 1-methyl ester

Product 1

HCID 684246972-Biphenyl-4-ylmethyl-succinic acid 4-tert-butyl ester 1-methyl ester

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-[1-biphenyl-4-yl-meth-(Z)-ylidene]-succinic acid 4-tert-butyl ester 1-methyl ester (410 mg, 1.163 mmol) in ethyl acetate (20 mL) is hydrogenated over Pt/C (40 mg) at 1 atm for 18 hours. The catalyst is filtered through Celite and the solvent is removed under reduced pressure to give 2-biphenyl-4-ylmethyl-succinic acid 4-tert-butyl ester 1-methyl ester. The enantiomers are separated by chiral HPLC.

Workup

  1. filtrationThe catalyst is filtered through Celite
  2. customthe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-8f45b771c9904f3dacf1450f53b94f17
Source dataset
uspto-grants-2014_09
Patent number
US08822534B2

Reaction notes

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