Sodium borohydride → N-[(1RS)-1-hydroxymethyl-2-(2-pyrazinyl)ethyl]acetamide

HRID 47764Notes

Reaction equation

[BH4-].[Na+].[C:3]([NH:6][CH:7]([CH2:13][C:14]1[CH:19]=[N:18][CH:17]=[CH:16][N:15]=1)[C:8](OCC)=[O:9])(=[O:5])[CH3:4]>C(O)C.O>[OH:9][CH2:8][CH:7]([NH:6][C:3](=[O:5])[CH3:4])[CH2:13][C:14]1[CH:19]=[N:18][CH:17]=[CH:16][N:15]=1

Participants

Conditions

Temperature: 20 °C

Procedure

2.8 g of sodium borohydride are added to a solution of 8.5 g of ethyl (2RS)-2-acetylamino-3-(2-pyrazinyl)propanoate in 100 cm3 of ethanol and the mixture is then stirred at a temperature in the region of 20° C. After 18 hours, the reaction medium is taken up in 50 cm3 of water and 100 cm3 of dichloromethane and the aqueous phase is concentrated under reduced pressure (1 kPa) at a temperature in the region of 40° C. 11 g of N-[(1RS)-1-hydroxymethyl-2-(2-pyrazinyl)-ethyl]acetamide are obtained in the form of a brown paste [1H NMR spectrum (300 MHz, (CD3)2SO-d6 with addition of a few drops of CD3COOD-d4 δ in ppm): 1.71 (s: 3H); 2.81 (dd, J=14.5 and 9 Hz: 1H); 3.03 (dd, J=14.5 and 5 Hz: 1H); 3.35 (dd, J=11 and 6 Hz); 3.42 (dd, J=11 and 5 Hz: 1H); 4.11 (mt: 1H); 7.75 (residual d, J=8.5 Hz: 0.5H); 8.45 (d, J=2.5 Hz: 1H); 8.50 (broad s: 1H); 8.53 (mt: 1H)]).

Workup

concentration100 cm3 of dichloromethane and the aqueous phase is concentrated under reduced pressure (1 kPa) at a temperature in the region of 40° C

Sources & evidence

ORD record: ord-6b145cc4f362407e8cf44431c7156d5a
Source dataset: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06699895B2

Reaction notes

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