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

HRID 479330Notes

Reaction equation

HRID 479330 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])[C@H:13]([C@@H:15]([C:17]([OH:19])=[O:18])[OH:16])[OH:14]>CCO>[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[CH2:11][CH2:10][CH2:9][C@H:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH2:2]1

Participants

4

Reactant 2

HCID 98969Ethyl nipecotateHCID 439655D-Tartaric acid

Product 1

HCID 14183617Ethyl (S)-3-Piperidinecarboxylate D-TartrateYield 28,091%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl nipecotate (70.2 g, 0.446 mmol) and D-tartaric acid (67.0 g, 1.0 eq.) were dissolved in hot 95% EtOH (350 mL). The resulting solution was cooled to room temperature, filtered, and the crystals washed with ice-cold 95% EtOH. The product was then recrystallized from 95% EtOH (550 mL) to give ethyl (S)-nipecotate D-tartrate (38.5 g, 56% yield). The salt (38.5 g) was dissolved in water (300 mL), cooled to 0° C., and 3M NaOH was added until the pH was 9-10. The resulting solution was extracted with CH2Cl2 (5×100 mL) and the combined organics dried over Na2SO4, filtered, and concentrated under reduced pressure to give Compound (41) as a clear oil (19 g, 89% yield). CIMS: MH+=158.

Workup

  1. filtrationfiltered
  2. washthe crystals washed with ice-cold 95% EtOH
  3. customThe product was then recrystallized from 95% EtOH (550 mL)

Sources & evidence

ORD record
ord-b5e7059d29be48ee82a53384abe749a5
Source dataset
uspto-grants-2003_11
Patent number
US06645966B2

Reaction notes

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