Sodium borohydride → N-[(1S)-2-hydroxy-1-(3-nitrobenzyl)ethyl]acetamide

HRID 1280635Notes

Reaction equation

HRID 1280635 reaction equation
[C:1]([NH:4][C@@H:5]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[CH:13]=1)[C:6](OCC)=[O:7])(=[O:3])[CH3:2].[BH4-].[Na+]>C(O)C>[OH:7][CH2:6][C@@H:5]([NH:4][C:1](=[O:3])[CH3:2])[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[CH:13]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 53755981HCID 53755981, compound

Product 1

HCID 69698133N-[(1S)-2-hydroxy-1-(3-nitrobenzyl)ethyl]acetamideYield 95.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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.

Sources & evidence

ORD record
ord-d0a4d5fe22804d8c881f789b083cab46
Source dataset
uspto-grants-2002_09
Patent number
US06451821B1

Reaction notes

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