Sodium borohydride → Diethyl 5-(2-bromo-1-hydroxyethyl)-1,6-dihydro-6-oxo-2,3-pyridinedicarboxylate

HRID 365088Notes

Reaction equation

HRID 365088 reaction equation
[BH4-].[Na+].[Br:3][CH2:4][C:5]([C:7]1[C:12](=[O:13])[NH:11][C:10]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:9]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:8]=1)=[O:6]>>[Br:3][CH2:4][CH:5]([C:7]1[C:12](=[O:13])[NH:11][C:10]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:9]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:8]=1)[OH:6]

Participants

3

Reactant 2

HCID 4311764Sodium borohydride2×HCID 13752509Diethyl 5-(bromoacetyl)-1,6-dihydro-6-oxo-2,3-pyridinedicarboxylate

Product 1

HCID 13752510Diethyl 5-(2-bromo-1-hydroxyethyl)-1,6-dihydro-6-oxo-2,3-pyridinedicarboxylate

Procedure

Sodium borohydride (2.54 g, 0.066 mol) is added in portions over a 30 minute period to a stirred suspension of diethyl 5-(bromoacetyl)-1,6-dihydro-6-oxo-2,3-pyridinedicarboxylate (57.2 g, 0.159 mol) at 10°-20° C. Upon completion of the sodium borohydride addition, the reaction mixture is stirred while attaining room temperature. Ice (100 g) is added and the mixture stirred until the ice has melted. The mixture is then concentrated in vacuo and the residue crystallized twice from an ethyl acetate-hexane mixture to give pure diethyl 5-(2-bromo-1-hydroxyethyl)-1,6-dihydro-6-oxo-2,3-pyridinedicarboxylate mp 134°-138° C.

Workup

  1. customwhile attaining room temperature
  2. concentrationThe mixture is then concentrated in vacuo
  3. customthe residue crystallized twice from an ethyl acetate-hexane mixture

Sources & evidence

ORD record
ord-802206038dca4b6cb8dce3fce2ccd25e
Source dataset
uspto-grants-1986_08
Patent number
US04608079

Reaction notes

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