Trifluoroacetic acid → 3-Methylpiperidine-3-carboxylic acid

HRID 69906Notes

Reaction equation

HRID 69906 reaction equation
C(O)(C(F)(F)F)=O.C(OC([N:15]1[CH2:20][CH2:19][CH2:18][C:17]([CH3:24])([C:21]([OH:23])=[O:22])[CH2:16]1)=O)(C)(C)C>C(Cl)Cl>[CH3:24][C:17]1([C:21]([OH:23])=[O:22])[CH2:18][CH2:19][CH2:20][NH:15][CH2:16]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 186197611-((Tert-butoxy)carbonyl)-3-methylpiperidine-3-carboxylic acid

Product 1

HCID 184196953-Methylpiperidine-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA was added to a solution of 1-(tert-butoxycarbonyl)-3-methylpiperidine-3-carboxylic acid (1 eq) in CH2Cl2 (0.5 M). After stirring for 3 h at it the reaction mixture was concentrated in vacuo and azeotroped once with toluene to give 3-methylpiperidine-3-carboxylic acid (TFA salt). The crude product was used for the next step without further purification.

Workup

  1. concentrationwas concentrated in vacuo
  2. customazeotroped once with toluene

Sources & evidence

ORD record
ord-952089f710114625848889319359b2da
Source dataset
uspto-grants-2014_09
Patent number
US08822497B2

Reaction notes

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