Tert-butyl 4-(pyridin-4-ylmethyl)piperidine-1-carboxylate → 4-Piperidin-4-ylmethyl-piperidine-1-carboxylic acid t-butyl ester
Reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][CH:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)=[CH:3][CH:2]=1>C(O)C.C(O)(=O)C.[Pt]=O>[NH:1]1[CH2:2][CH2:3][CH:4]([CH2:7][CH:8]2[CH2:9][CH2:10][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:12][CH2:13]2)[CH2:5][CH2:6]1Participants
5
Procedure
1,1-Dimethylethyl 4-(4-pyridinylmethyl)-1-piperidinecarboxylate (may be prepared as described in Description 1) (11.4 g) was dissolved in ethanol (200 ml) and acetic acid (2.36 ml). Platinum oxide (2 g) was added under a blanket of argon, and the reaction shaken under hydrogen at 50 psi for 18 h. After carefully filtering off the platinum catalyst, the solvent was evaporated and the residue redissolved in ethyl acetate (50 ml) and washed with saturated sodium hydrogen carbonate solution (50 ml). The aqueous phase was extracted into ethyl acetate (2×50 ml) and the combined organics dried (Na2SO4) and evaporated to give the title compound (D2) as white solid (9.4 g).
Workup
- filtrationAfter carefully filtering off the platinum catalyst
- customthe solvent was evaporated
- dissolutionthe residue redissolved in ethyl acetate (50 ml)
- washwashed with saturated sodium hydrogen carbonate solution (50 ml)
- extractionThe aqueous phase was extracted into ethyl acetate (2×50 ml)
- dry with materialthe combined organics dried (Na2SO4)
- customevaporated
Sources & evidence
- ORD record
- ord-076c84a7209e426891f0bab459b08db4
- Source dataset
- uspto-grants-2009_12
- Patent number
- US07638631B2
Reaction notes
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