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

HRID 353392

Reaktionsgleichung

Reaktionsgleichung von HRID 353392
[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]>CO.[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]

Komponenten

4

Edukt 1

HCID 10803584(R)-2-[2-(tert-butoxy)-2-oxoethyl]-5-phenylpentanoic acid

Produkt 1

HCID 9835906(2R)-2-[2-(tert-butoxy)-2-oxoethyl]-5-cyclohexylpentanoic acidAusbeute 89,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23948RhodiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of (R)-2-[2-(tert-butoxy)-2-oxoethyl]-5-phenylpentanoic acid (2.2 g, 7.5 mmol) and 5% rhodium on carbon (0.22 g) in methanol (220 ml) was stirred at 20-25° C., under hydrogen (10 atmospheres, 150 p.s.i.) for 24 hours and then filtered through celite. The filtrate was concentrated in vacuo to leave the title compound as an oil (2.0 g, 89% yield, 95% pure by NMR).

Aufarbeitung

  1. filtrationfiltered through celite
  2. concentrationThe filtrate was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-372bf99ee7364c4c8f036a39a88b8ed6
Quelldatensatz
uspto-grants-2004_06
Patentnummer
US06750363B2

Verknüpfte Notizen

Wird geladen…