Trifluoroacetic acid → HCID 67751520, compound

Participants

Reaction Conditions

Reaction Steps

Trifluoroacetic acid (3 ml) was added to 1-t-butyloxycarbonyl-3-((3,5-dimethylphenyl)methyloxy)-2-phenylpiperidine (800 mg Example 2d) under nitrogen and the solution was stirred at 23° C. for 1 h. Excess trifluoroacetic acid was removed in vacuo, and the residue was partitioned between 2M sodium hydroxide and dichloromethane. The layers were separated, and the aqueous phase was extracted twice with dichloromethane. The combined organic phases were dried (K2CO3) and concentrated to leave a clear, colourless oil. Purification on silica gel (CH2Cl2 /MeOH/NH3 97:3:0.5 then CH2Cl2 /MeOH 95:5→90:10→80:20) provided, in order of elution, trans-3-((3,5-dimethylphenyl)methyloxy)-2-phenylpiperidine as a colourless oil. 1H NMR (CDCl3) δ7.5-7.24 (m), 6.80 (s), 6.50 (s), 4.20 (d, J=11 Hz), 3.98 (d, J=11 Hz), 3.48 (d, J=8.4 Hz), 3.32 (ddd, J=4.2, 9.8, 9.8 Hz), 3.08 (m), 2.70 (ddd, J=2.8, 12.6, 12.6 Hz), 2.10 (m), 2.19 (s), 1.84-1.4 (m), and cis-3-((3,5-dimethylphenyl)methyloxy)-2-phenylpipieridine as a colourless oil. 1H NMR (CDCl3) δ7.4-7.2 (m), 6.55 (s), 6.31 (s), 4.33 (d, J=12.2 Hz), 4.10 (d, J=12.2 Hz), 3.78 (s), 3.63 (s), 3.26 (app. dt, J=2.16, 2.16, 12.5 Hz), 2.82 (ddd, J=3.0, 3.0, 12.6 Hz), 2.20 (s), 1.86 (m), 1.62 (m), 1.48 (m). m/z (CI+) 296(MH).

Provenance & Evidence