Ethyl nipecotate → Ethyl (S)-3-Piperidinecarboxylate D-Tartrate

HRID 1872665Notes

Reaction equation

HRID 1872665 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH:3]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:2]1.[C:12]([OH:21])(=[O:20])[C@H:13]([C@@H:15]([C:17]([OH:19])=[O:18])[OH:16])[OH:14]>C(O)C>[C:17]([C@H:15]([C@@H:13]([C:12]([OH:21])=[O:20])[OH:14])[OH:16])([OH:19])=[O:18].[NH:1]1[CH2:6][CH2:5][CH2:4][C@H:3]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:2]1

Participants

4

Reactant 2

HCID 98969Ethyl nipecotateHCID 439655D-Tartaric acid

Product 1

HCID 14183617Ethyl (S)-3-Piperidinecarboxylate D-Tartrate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 3-piperidinecarboxylate (200 g) was combined with (-)-D-tartaric acid (191 g) in hot 95% ethanol. The resulting precipitate was filtered and recrystallized six times from 95% ethanol to give (S)-ethyl 3-piperidinecarboxylate D-tartrate salt of high optical purity as determined by chiral HPLC analysis.

Workup

  1. filtrationThe resulting precipitate was filtered
  2. customrecrystallized six times from 95% ethanol

Sources & evidence

ORD record
ord-1d08548cf37c481bb76154176bc09be5
Source dataset
uspto-grants-2000_08
Patent number
US06110937

Reaction notes

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