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 2264357Notes

Reaction equation

HRID 2264357 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[CH:15]=[N:16][C:17]([N+:20]([O-])=O)=[CH:18][CH:19]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)C.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([C:14]2[CH:15]=[N:16][C:17]([NH2:20])=[CH:18][CH:19]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

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 100.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Dissolve 6-nitro-3′,6′-dihydro-2′H-[3,4]bipyridinyl-1′-carboxylic acid tert-butyl ester (1.89 g) in ethanol (123.80 mL). Hydrogenate with palladium on carbon (H-Cube instrument, 70 bar, 50° C., 1 mL/min) to afford 1.72 g of the title compound. MS (ES+): m/z=278 (M+H)+.

Sources & evidence

ORD record
ord-f6b2574d7119441d97975fa122b08aad
Source dataset
uspto-grants-2010_12
Patent number
US07855211B2

Reaction notes

Loading…