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

HRID 1280603Notes

Reaction equation

HRID 1280603 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 86584419ethyl (2R)-2-(acetylamino)-3-(3-nitrophenyl)propanoate

Product 1

HCID 69698954N-[(1R)-2-hydroxy-1-(3-nitrobenzyl)ethyl]acetamideYield 84%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A light suspension, under an inert atmosphere, of 1.4 g of ethyl (2R)-2-(acetylamino)-3-(3-nitrophenyl)propanoate in 13 cm3 of ethanol is cooled to a temperature of 20° C. and 0.29 g of sodium borohydride is then added thereto. The yellow solution obtained is stirred at room temperature for 18 hours. The reaction medium is then concentrated under reduced pressure (2 kPa) at a temperature in the region of 50° C., after which 10 cm3 of water are added and the mixture is extracted with twice 50 cm3 of ethyl acetate. The combined organic phases are dried over sodium sulfate, filtered and then concentrated under reduced pressure (2 kPa) at a temperature in the region of 40° C. 1 g of N-[(1R)-2-hydroxy-1-(3-nitrobenzyl)ethyl]-acetamide is obtained in the form of pale yellow crystals melting at 135° C. 1H NMR spectrum (250 MHz, (CD3)2SO-d6, δ in ppm): 1.75 (s: 3H); 2.74 (dd, J=14 and 9 Hz: 1H); 3.02 (dd, J=14 and 5 Hz: 1H); from 3.25 to 3.45 (mt: 2H); 3.96 (mt: 1H); 4.90 (broad s: 1H); 7.59 (t, J=8 Hz: 1H); 7.70 (broad d, J=8 Hz: 1H); 7.82 (d, J=8.5 Hz: 1H); from 8.05 to 8.15 (mt: 2H).

Workup

  1. additionis then added
  2. customThe yellow solution obtained
  3. concentrationThe reaction medium is then concentrated under reduced pressure (2 kPa) at a temperature in the region of 50° C.
  4. additionafter which 10 cm3 of water are added
  5. extractionthe mixture is extracted with twice 50 cm3 of ethyl acetate
  6. dry with materialThe combined organic phases are dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure (2 kPa) at a temperature in the region of 40° C

Sources & evidence

ORD record
ord-3db782abd9ab48b189fca268413cfdf8
Source dataset
uspto-grants-2002_09
Patent number
US06451821B1

Reaction notes

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