Trifluoroacetic acid → Nipecotic Acid

HRID 2079342Notes

Reaction equation

HRID 2079342 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([C:14]([OH:16])=[O:15])[CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH:8]1[CH2:13][CH2:12][CH2:11][CH:10]([C:14]([OH:16])=[O:15])[CH2:9]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 27356471-((Tert-butoxy)carbonyl)piperidine-3-carboxylic acid

Product 1

HCID 4498Nipecotic Acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(tert-butoxycarbonyl)piperidine-3-carboxylic acid (500 mg, 2.18 mmol) in CH2Cl2 (10 mL) was added TFA (5 ml). The reaction mixture was stirred for an hour. Excess TFA was removed under reduced pressure, and the piperidine-3-carboxylic acid was used without neutralization for the next step. LC/MS: m/z 1303 (M+H)+ at 0.35 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Workup

  1. customExcess TFA was removed under reduced pressure

Sources & evidence

ORD record
ord-a9cb8ed4454c438a8944f007dbfad919
Source dataset
uspto-grants-2011_04
Patent number
US07928107B2

Reaction notes

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