Trifluoroacetic acid → 4-Ethylpiperidine-4-carboxylic acid

HRID 2179756Notes

Reaction equation

HRID 2179756 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11]([CH2:17][CH3:18])([C:14]([OH:16])=[O:15])[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH2:17]([C:11]1([C:14]([OH:16])=[O:15])[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1)[CH3:18]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 221690971-[(Tert-butoxy)carbonyl]-4-ethylpiperidine-4-carboxylic acid

Product 1

HCID 509442034-Ethylpiperidine-4-carboxylic acidYield 112.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 1-(tert-butoxycarbonyl)-4-ethylpiperidine-4-carboxylic acid (above step 1, 4.5 g, 12.96 mmol) in DCM (50 ml) was cooled to 0° C. After ten minutes, trifluoro acetic acid (6.0 g) was added and stirred the reaction at room temperature for about 6 hours. Upon completion of the reaction (monitored by TLC), the reaction mixture was neutralized with saturated NaHCO3 and extracted with DCM. The organic layer was dried over Na2SO4 and concentrated under reduced pressure to furnish the title compound (2.3 g) as a light yellow liquid. 1H NMR (300 MHz, CDCl3): 1.48-1.58 (m, 2H); 2.14-2.18 (m, 2H); 2.64-2.73 (m, 2H); 2.86 (s, 2H); 3.01-3.07 (m, 4H); ES Mass: 158 (100%), [M+1].

Workup

  1. waitAfter ten minutes
  2. customthe reaction at room temperature for about 6 hours
  3. customUpon completion of the reaction (monitored by TLC)
  4. extractionextracted with DCM
  5. dry with materialThe organic layer was dried over Na2SO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f1e5a180c4c94263a3190a108b1fa316
Source dataset
uspto-grants-2015_06
Patent number
US09067966B2

Reaction notes

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