Trifluoroacetic acid → HCID 59371493, compound

HRID 2095431Notes

Reaction equation

HRID 2095431 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][C@@H:12]1[CH2:17][CH2:16][CH2:15][N:14](C(OC(C)(C)C)=O)[CH2:13]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl.O>[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][C@@H:12]1[CH2:17][CH2:16][CH2:15][NH:14][CH2:13]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59371550HCID 59371550, compound

Product 1

HCID 59371493HCID 59371493, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 21908982Water methylene chlorideSolvent

Procedure

To a solution of tert-butyl 3(S)-[3-(benzyloxy)propyl]piperidine-1-carboxylate (280 mg, 0.84 mmol) in CH2Cl2/H2O (6 mL/0.5 mL) was added CF3COOH (1.92 g, 16.8 mmol, 20 equiv.) at 0° C. under N2. The solution was stirred overnight at room temperature. After concentration under reduced pressure, water was added, and the solution was washed with hexane. The aqueous phase was basified with saturated NaHCO3 solution and extracted with EtOAc. The combined organic layers were washed with brine and dried over Na2SO4. The solvent was removed in vacuo to give 3(S)-[3-(benzyloxy)propyl]piperidine (190 mg, 97%) as a yellow oil. LC-MS (ESI) m/z 234 (M+H+).

Workup

  1. concentrationAfter concentration under reduced pressure, water
  2. additionwas added
  3. washthe solution was washed with hexane
  4. extractionextracted with EtOAc
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over Na2SO4
  7. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-82d05e8b5be944a4bd7073f9b29f7d8f
Source dataset
uspto-grants-2013_05
Patent number
US08445684B2

Reaction notes

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