Reaktion #219980

ord-9751ade2cea64cabb0c400d8d50b2ecf

Reaktionsgleichung

C=CC(=O)[C@H](Cc1cc(F)cc(F)c1)NC(=O)OC(C)(C)C
Ketone
C=CC(=O)[C@H](Cc1cc(F)cc(F)c1)NC(=O)OC(C)(C)C
Tert-butyl (1S)-1-(3,5-difluorobenzyl)-2-oxobut-3-enylcarbamate
[BH4-].[Ce+3].[Cl-].[Cl-].[Cl-].[Na+]
sodium borohydride cerium chloride
→
C=CC(O)[C@H](Cc1cc(F)cc(F)c1)NC(=O)OC(C)(C)C
alcohol
C=CC(O)[C@H](Cc1cc(F)cc(F)c1)NC(=O)OC(C)(C)C
Tert-butyl (1S)-1-(3,5-difluorobenzyl)-2-hydroxybut-3-enylcarbamate

Edukte

C=CC(=O)[C@H](Cc1cc(F)cc(F)c1)NC(=O)OC(C)(C)C
Ketone
C=CC(=O)[C@H](Cc1cc(F)cc(F)c1)NC(=O)OC(C)(C)C
Tert-butyl (1S)-1-(3,5-difluorobenzyl)-2-oxobut-3-enylcarbamate
[BH4-].[Ce+3].[Cl-].[Cl-].[Cl-].[Na+]
sodium borohydride cerium chloride

Reagenzien

Keine

Lösungsmittel

CO
methanol

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Vorschrift

Ketone (2) was reduced with sodium borohydride/cerium chloride (Luche conditions) in methanol at 0° C. to provide the allylic alcohol 3 as a mixture of alcohol epimers (white solid).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07388118B2uspto-grants-2008_06