tert-Butyl 6-nitro-3',6'-dihydro-[3,4'-bipyridine]-1'(2'H)-carboxylate → tert-Butyl 4-(6-aminopyridin-3-yl)piperidine-1-carboxylate
Reaction equation
[N+:1]([C:4]1[N:9]=[CH:8][C:7]([C:10]2[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH:11]=2)=[CH:6][CH:5]=1)([O-])=O>CCO.C(OCC)(=O)C.[Pd]>[C:19]([O:18][C:16]([N:13]1[CH2:12][CH2:11][CH:10]([C:7]2[CH:8]=[N:9][C:4]([NH2:1])=[CH:5][CH:6]=2)[CH2:15][CH2:14]1)=[O:17])([CH3:22])([CH3:20])[CH3:21]Participants
Procedure
In a 500 mL round-bottomed flask, tert-butyl 4-(6-nitropyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxylate (4.9 g, 16.0 mmol, Eq: 1.00) in EtOH (300 ml) and ethyl acetate (75 ml) was combined with palladium on carbon (1.32 g, 1.24 mmol, Eq: 0.0773). The reaction mixture was evacuated twice with hydrogen and then stirred with a hydrogen-filled balloon overnight. LC/MS analysis showed that the reaction was complete. The reaction mixture was purged with nitrogen and filtered through celite. The celite cake was washed several times with EtOAc. To the colorless combined filtrate and washes was added CH2Cl2 and the solution was evaporated to dryness. CH2Cl2 was added again and the solution was concentrated in vacuo to afford quantitative yield of the desired product. (M+H)+=278 m/e.
Workup
- customThe reaction mixture was evacuated twice with hydrogen
- additionfilled balloon overnight
- customThe reaction mixture was purged with nitrogen
- filtrationfiltered through celite
- washThe celite cake was washed several times with EtOAc
- additionwas added CH2Cl2
- customthe solution was evaporated to dryness
- additionCH2Cl2 was added again
- concentrationthe solution was concentrated in vacuo
Sources & evidence
- ORD record
- ord-79ad051008864e70a114a56bca159ad1
- Source dataset
- uspto-grants-2014_11
- Patent number
- US08889682B2
Reaction notes
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