Reaktion #158058

ord-8f45b771c9904f3dacf1450f53b94f17

Reaktionsgleichung

COC(=O)/C(=C\c1ccc(-c2ccccc2)cc1)CC(=O)OC(C)(C)C
2-[1-biphenyl-4-yl-meth-(Z)-ylidene]-succinic acid 4-tert-butyl ester 1-methyl ester
→
COC(=O)C(CC(=O)OC(C)(C)C)Cc1ccc(-c2ccccc2)cc1
2-biphenyl-4-ylmethyl-succinic acid 4-tert-butyl ester 1-methyl ester

Edukte

COC(=O)/C(=C\c1ccc(-c2ccccc2)cc1)CC(=O)OC(C)(C)C
2-[1-biphenyl-4-yl-meth-(Z)-ylidene]-succinic acid 4-tert-butyl ester 1-methyl ester

Reagenzien

[Pt]
Pt/C

Lösungsmittel

CCOC(C)=O
ethyl acetate

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    FiltrationThe catalyst is filtered through Celite
  2. 2
    Sonstigethe solvent is removed under reduced pressure

Vorschrift

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.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08822534B2uspto-grants-2014_09