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
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.
Workup
- filtrationThe reaction was then filtered
- customthe filtrate was evaporated
- additionThe residue was diluted with ethyl acetate and 1N hydrochloric acid
- customThe aqueous phase was collected
- extractionextracted with ethyl acetate
- dry with materialThe combined organic phases were dried over anhydrous magnesium sulfate
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-3169c6071a4e4990a142bbb95ba9cf79
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08343999B2
Reaction notes
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