Tert-butyl 4-cyano-4-phenylpiperidine-1-carboxylate → Tert-butyl 4-(aminomethyl)-4-phenylpiperidine-1-carboxylate
Reaction equation
[C:1]([C:3]1([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1)#[N:2]>C(O)(=O)C.C(O)C.[Pt]=O>[NH2:2][CH2:1][C:3]1([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:14])([CH3:15])[CH3:13])=[O:10])[CH2:5][CH2:4]1Participants
4
Procedure
Tert-butyl 4-cyano-4-phenylpiperidine-1-carboxylate (2.6 g, 9.08 mmol) was dissolved in 15% acetic acid/ethanol and hydrogenated at 50 psi over platinum oxide (0.052 g) for a week. HPLC showed only 50% conversion and the reaction was resubmitted to the same conditions and hydrogenated for 4 more days. The reaction was then filtered and the filtrate was evaporated. The residue was diluted with ethyl acetate and 1N hydrochloric acid. The aqueous phase was collected, basified with sodium carbonate and extracted with ethyl acetate. The combined organic phases were dried over anhydrous magnesium sulfate, filtered and concentrated to give the title material (0.835 g, 32%) as an oil which was used as such for the next reaction. LC/MS (M-(t-Bu)+H)+: 235. HPLC ret. time (Condition B): 1.322 min.