tert-butyl 4-(2-(N-methoxy-N-methylcarbamoyl)-6-fluorophenyl)-5,6-dihydropyridine-1(2H)-carboxylate → tert-Butyl 4-(2-(N-methoxy-N-methylcarbamoyl)-6-fluorophenyl)piperidine-1-carboxylate
Reaction equation
[CH3:1][O:2][N:3]([CH3:26])[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([F:12])[C:7]=1[C:13]1[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH:14]=1)=[O:5]>CCO.O=[Pt]=O>[CH3:1][O:2][N:3]([CH3:26])[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([F:12])[C:7]=1[CH:13]1[CH2:14][CH2:15][N:16]([C:19]([O:21][C:22]([CH3:24])([CH3:23])[CH3:25])=[O:20])[CH2:17][CH2:18]1)=[O:5]Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of tert-butyl 4-(2-(N-methoxy-N-methylcarbamoyl)-6-fluorophenyl)-5,6-dihydropyridine-1(2H)-carboxylate (450 mg, 1.235 mmol) and PtO2 (180 mg) in EtOH (19 mL) was shaken in a Parr flask for 1 h15 under 51 psi of H2. The reaction was monitored by LC/MS. Unreacted SM was detected, so another 150 mg of PtO2 (total: 450 mg, 30 wt %) was then added and the mixture was hydrogenated under 50 psi for another 3 h. Mostly desired product was detected after 4 h by LC/MS (Rt=2.83 min). The catalyst was filtered off and the solution was concentrated in vacuo to yield 435 mg of tert-butyl 4-(2-(N-methoxy-N-methylcarbamoyl)-6-fluorophenyl)piperidine-1-carboxylate as a clear thick oil which was used as is for the next step. LC/MS ES+1: 367.38.
Sources & evidence
- ORD record
- ord-086d53ecf2bb4e56bdc4a8d37d640eec
- Source dataset
- uspto-grants-2012_04
- Patent number
- US08163737B2
Reaction notes
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