Sodium Hydroxide → Ethyl (3S)-piperidine-3-carboxylate

HRID 394046Notes

Reaction equation

HRID 394046 reaction equation
C(O)(=O)[C@H]([C@@H](C(O)=O)O)O.[NH:11]1[CH2:16][CH2:15][CH2:14][C@H:13]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:12]1.[OH-].[Na+]>>[NH:11]1[CH2:16][CH2:15][CH2:14][C@H:13]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:12]1

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 14183617Ethyl (S)-3-Piperidinecarboxylate D-Tartrate

Product 1

HCID 187784Ethyl (3S)-piperidine-3-carboxylateYield 112.8%

Procedure

To 13.0 g of ethyl (3S)-3-piperidinecarboxylate D(−)-tartarate which was synthesized following the method of P. Magnus, et al. [J. Org. Chem. Vol. 56, 1166-1170 (1991)], 3N aqueous sodium hydroxide solution was added to render the former basic, followed by extraction with chloroform and drying over anhydrous magnesium sulfate. Distilling the solvent off under reduced pressure, 7.50 g of the title compound was obtained.

Workup

  1. extractionfollowed by extraction with chloroform
  2. dry with materialdrying over anhydrous magnesium sulfate
  3. distillationDistilling the solvent off under reduced pressure

Sources & evidence

ORD record
ord-2634489c1dd6442fbb237c8936f4cd17
Source dataset
uspto-grants-2004_10
Patent number
US06809108B1

Reaction notes

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