Trifluoroacetic acid → (2S)-2-phenyl-3-piperidone

HRID 1935685Notes

Reaction equation

HRID 1935685 reaction equation
FC(F)(F)C(O)=O.C(OC([N:15]1[CH2:20][CH2:19][CH2:18][C:17](=[O:21])[C@@H:16]1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=O)(C)(C)C>C(Cl)Cl>[C:22]1([C@H:16]2[C:17](=[O:21])[CH2:18][CH2:19][CH2:20][NH:15]2)[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 10956740(2S)-1-tert-butoxycarbonyl-2-phenylpiperidin-3-one

Product 1

HCID 9812895(2S)-2-phenyl-3-piperidone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (4 mL) is added to a stirred, cooled (0° C.) solution of (2S)- 1-tert-butoxycarbonyl-2-phenylpiperidin-3-one (40 mg) in methylene chloride (2 mL) and the mixture is stirred at room temperature for 3 h. The solvent is evaporated under reduced pressure and the residue is partitioned between aqueous saturated sodium bicarbonate (50 ml) and ethyl acetate (3×50 ml). The combined organic fractions are washed with brine (50 ml), dried (MgSO4) and evaporated in vacuo to give (2S)-2-phenylpiperidin-3-one.

Workup

  1. customThe solvent is evaporated under reduced pressure
  2. customthe residue is partitioned between aqueous saturated sodium bicarbonate (50 ml) and ethyl acetate (3×50 ml)
  3. washThe combined organic fractions are washed with brine (50 ml)
  4. dry with materialdried (MgSO4)
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-8f5cc964fdcd4db58dd017c37871a0a1
Source dataset
uspto-grants-2002_05
Patent number
US06388083B2

Reaction notes

Loading…