Reaktion #76014

ord-1cd3757d15404d4dae993ba458c8f512

Reaktionsgleichung

CCOC(=O)[C@H](Cc1cccc([N+](=O)[O-])c1)NC(C)=O
ethyl (2S)-2-(acetylamino)-3-(3-nitrophenyl)propanoate
[BH4-].[Na+]
sodium borohydride
→
CC(=O)N[C@H](CO)Cc1cccc([N+](=O)[O-])c1
N-[(1S)-2-hydroxy-1-(3-nitrobenzyl)-ethyl]acetamide
Ausbeute 95.4%

Edukte

CCOC(=O)[C@H](Cc1cccc([N+](=O)[O-])c1)NC(C)=O
ethyl (2S)-2-(acetylamino)-3-(3-nitrophenyl)propanoate
[BH4-].[Na+]
sodium borohydride
—
solid

Reagenzien

Keine

Lösungsmittel

CCO
ethanol

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Vorschrift

The process is performed as in Example 2, starting with 7.15 g of ethyl (2S)-2-(acetylamino)-3-(3-nitrophenyl)propanoate and 1.46 g of sodium borohydride in 70 cm3 of ethanol. After an identical work-up, 5.8 g of N-[(1S)-2-hydroxy-1-(3-nitrobenzyl)-ethyl]acetamide are obtained in the form of a white solid melting at 131° C.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06699895B2uspto-grants-2004_03