Ethyl (R)-Nipecotate L-Tartrate → ethyl (3R)-piperidine-3-carboxylate

HRID 1862534Notes

Reaction equation

HRID 1862534 reaction equation
C(O)(=O)[C@@H]([C@H](C(O)=O)O)O.[CH2:11]([O:13][C:14]([C@@H:16]1[CH2:21][CH2:20][CH2:19][NH:18][CH2:17]1)=[O:15])[CH3:12]>C(OCC)(=O)C.O.[OH-].[Na+]>[CH2:11]([O:13][C:14]([C@@H:16]1[CH2:21][CH2:20][CH2:19][NH:18][CH2:17]1)=[O:15])[CH3:12]

Participants

5

Reactant 1

HCID 14183616Ethyl (R)-Nipecotate L-Tartrate

Product 1

HCID 185582ethyl (3R)-piperidine-3-carboxylateYield 98.7%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of (R)-3-piperidinecarboxylic acid ethyl ester L-tartaric acid salt (30.3 g) in ethyl acetate (300 ml) and water (60 ml), 12% aqueous sodium hydroxide was added to adjust pH to 13. Aqueous layer was extracted with ethyl acetate (60 ml) two times and combined organic layer was dried with sodium sulfate (8 g). Organic layer was concentrated in vacuo to give (R)-3-piperidinecarboxylic acid ethyl ester (15.3 g).

Workup

  1. extractionAqueous layer was extracted with ethyl acetate (60 ml) two times and combined organic layer
  2. dry with materialwas dried with sodium sulfate (8 g)
  3. concentrationOrganic layer was concentrated in vacuo

Sources & evidence

ORD record
ord-613dd7e6791d48689e66b64bf5978311
Source dataset
uspto-grants-2003_03
Patent number
US06538007B1

Reaction notes

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