Trifluoroacetic acid → HCID 67751520, compound

HRID 2210689Notes

Reaction equation

HRID 2210689 reaction equation
FC(F)(F)C(O)=O.C(OC([N:15]1[CH2:20][CH2:19][CH2:18][CH:17]([O:21][CH2:22][C:23]2[CH:28]=[C:27]([CH3:29])[CH:26]=[C:25]([CH3:30])[CH:24]=2)[CH:16]1[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=O)(C)(C)C>>[CH3:29][C:27]1[CH:28]=[C:23]([CH2:22][O:21][C@@H:17]2[CH2:18][CH2:19][CH2:20][NH:15][C@H:16]2[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:24]=[C:25]([CH3:30])[CH:26]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 19379336HCID 19379336, compound

Product 1

HCID 67751520HCID 67751520, compound

Conditions

Temperature
23 °C

Procedure

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).

Workup

  1. customExcess trifluoroacetic acid was removed in vacuo
  2. customthe residue was partitioned between 2M sodium hydroxide and dichloromethane
  3. customThe layers were separated
  4. extractionthe aqueous phase was extracted twice with dichloromethane
  5. dry with materialThe combined organic phases were dried (K2CO3)
  6. concentrationconcentrated
  7. customto leave a clear, colourless oil
  8. customPurification on silica gel (CH2Cl2 /MeOH/NH3 97:3:0.5

Sources & evidence

ORD record
ord-264b883211ea47978b6fb89ad050f649
Source dataset
uspto-grants-1995_10
Patent number
US05459270

Reaction notes

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