Trifluoroacetic acid → Benzyl piperidine-3-carboxylate

HRID 602126Notes

Reaction equation

HRID 602126 reaction equation
FC(F)(F)C(O)=O.C(OC([N:15]1[CH2:30][CH2:29][CH2:28][CH:17]([C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:19])[CH2:16]1)=O)(C)(C)C>ClCCl>[NH:15]1[CH2:30][CH2:29][CH2:28][CH:17]([C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:19])[CH2:16]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 20723878Benzyl 1-Boc-piperidine-3-carboxylate

Product 1

HCID 13419237Benzyl piperidine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (43 mL, 558 mmol) was added to benzyl 1-(tert-butoxycarbonyl)nipecotate (7.11 g, 22.3 mmol) in dichloromethane (20 mL). The mixture was stirred for 3 hours. Subsequently, the reaction mixture was concentrated and water was added to the residue, followed by addition of 1 mol/L aqueous sodium hydroxide solution to make the mixture basic. The mixture was then extracted with ethyl acetate. The organic layer washed with brine and was dried over sodium sulfate. The solvent was evaporated to give 5.97 g (quant.) of the desired compound as a yellow oil.

Workup

  1. concentrationSubsequently, the reaction mixture was concentrated
  2. additionwater was added to the residue
  3. additionfollowed by addition of 1 mol/L aqueous sodium hydroxide solution
  4. extractionThe mixture was then extracted with ethyl acetate
  5. washThe organic layer washed with brine
  6. dry with materialwas dried over sodium sulfate
  7. customThe solvent was evaporated

Sources & evidence

ORD record
ord-139d2dd9afb445229f6e8c7ed36bbaa0
Source dataset
uspto-grants-2011_03
Patent number
US07902367B2

Reaction notes

Loading…