Hydrochloric Acid → (-)-Nipecotic acid

HRID 931196Notes

Reaction equation

HRID 931196 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH2:11][C@@H:10]([C:14]([OH:16])=[O:15])[CH2:9]1)=O)(C)(C)C.Cl>ClCCl.O1CCOCC1>[NH:8]1[CH2:13][CH2:12][CH2:11][C@@H:10]([C:14]([OH:16])=[O:15])[CH2:9]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 6435161-(1,1-Dimethylethyl) (3R)-1,3-piperidinedicarboxylate

Product 1

HCID 1796510(-)-Nipecotic acid

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
30 °C

Procedure

To a solution of (R)-1-(tert-butoxycarbonyl)piperidine-3-carboxylic acid (12.25 mmol) in dichloromethane (84 mL) was added a solution of hydrogen chloride in 1,4-dioxane (28 mL, 4M). The reaction mixture was stirred at 30° C. for 2 h. The solvent was removed under reduced pressure to afford (R)-piperidine-3-carboxylic acid which was used without further purification.

Workup

  1. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-5fd8378b65ea47ea994e7fedc7b081c9
Source dataset
uspto-grants-2016_03
Patent number
US09296745B2

Reaction notes

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