2,3-Dihydroxybutanedioic Acid → Ethyl nipecotate

HRID 1588000Notes

Reaction equation

HRID 1588000 reaction equation
[NH:1]1[CH2:11][CH2:10][CH2:9][CH:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH2:2]1.[C:12]([OH:21])(=[O:20])[CH:13]([CH:15]([C:17]([OH:19])=[O:18])[OH:16])[OH:14]>C(O)C>[C:17]([CH:15]([CH:13]([C:12]([O-:21])=[O:20])[OH:14])[OH:16])([O-:19])=[O:18].[NH:1]1[CH2:11][CH2:10][CH2:9][CH:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH2:2]1

Participants

5

Reactant 2

HCID 8752,3-Dihydroxybutanedioic AcidHCID 98969Ethyl nipecotate

Product 2

HCID 98969Ethyl nipecotateYield 61.1%HCID 38061142,3-Dihydroxybutanedioate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(±)-Ethyl nipecotate (70.16 g, 71ml) and (+)-tartaric acid (67 g) were dissolved in hot 95% ethanol (350 ml). The resulting solution was allowed to slowly cool to room temperature and refrigerated overnight. The crystals were filtered, washed with cold ethanol, and recrystallized from 95% ethanol (550 ml), cooling as before to give the (+)-tartrate salt of (+)-ethyl nipecotate (42.9 g). M.p. 155-156° C.

Workup

  1. filtrationThe crystals were filtered
  2. washwashed with cold ethanol
  3. customrecrystallized from 95% ethanol (550 ml)
  4. temperaturecooling as before

Sources & evidence

ORD record
ord-eb88d765859d4b9f90352231acdfeb21
Source dataset
uspto-grants-1993_06
Patent number
US05220016

Reaction notes

Loading…