tert-Butyl 6-nitro-3',6'-dihydro-[3,4'-bipyridine]-1'(2'H)-carboxylate → tert-Butyl 4-(6-aminopyridin-3-yl)piperidine-1-carboxylate

HRID 449618Notes

Reaction equation

HRID 449618 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]>[NH2:1][C:4]1[N:9]=[CH:8][C:7]([CH:10]2[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]2)=[CH:6][CH:5]=1

Participants

5

Reactant 1

HCID 49840377tert-Butyl 6-nitro-3',6'-dihydro-[3,4'-bipyridine]-1'(2'H)-carboxylate

Product 1

HCID 49839963tert-Butyl 4-(6-aminopyridin-3-yl)piperidine-1-carboxylateYield 110.6%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

In a 250 mL round-bottomed flask, tert-butyl 4-(6-nitropyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxylate (632 mg, 2.07 mmol, Eq: 1.00) in EtOH (25.0 ml) and ethyl acetate (10 ml) was combined with palladium on carbon (66.1 mg, 62.1 μmol, Eq: 0.03). The mixture was evacuated twice with hydrogen and then stirred with a hydrogen-filled balloon for 22 h. The hydrogen was replaced with nitrogen. The solution was filtered through celite. The celite was washed several times with EtOAc. Concentrated in vacuo to give tert-butyl 4-(6-aminopyridin-3-yl)piperidine-1-carboxylate (635 mg, quantitative yield). LC/MS-ESI observed [M+H]+ 278.

Workup

  1. customThe mixture was evacuated twice with hydrogen
  2. additionfilled balloon for 22 h
  3. filtrationThe solution was filtered through celite
  4. washThe celite was washed several times with EtOAc
  5. concentrationConcentrated in vacuo

Sources & evidence

ORD record
ord-2ee86ad4574d45c884e40547c8e2e2ab
Source dataset
uspto-grants-2013_07
Patent number
US08481540B2

Reaction notes

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