tert-Butyl 5',6'-dihydro-[2,4'-bipyridine]-1'(2'H)-carboxylate → tert-Butyl 4-(pyridin-2-yl)piperidine-1-carboxylate

HRID 406486Notes

Reaction equation

HRID 406486 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH:8]=1>C(O)C.C(O)(=O)C.[Pd]>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]1[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]1

Participants

5

Reactant 1

HCID 16094711tert-Butyl 5',6'-dihydro-[2,4'-bipyridine]-1'(2'H)-carboxylate

Product 1

HCID 11108143tert-Butyl 4-(pyridin-2-yl)piperidine-1-carboxylateYield 100%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

Tert-butyl 4-(pyridin-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate (0.150 g, 0.576 mmol) was dissolved in ethanol (2 mL) and acetic acid (0.2 mL). The reaction mixture was hydrogenated with Pd/C (10%) in an H-cubemapparatus at about 60° C. for about 3 minutes. The solvent was removed in vacuo to give tert-butyl 4-(pyridin-2-yl)piperidine-1-carboxylate (0.151 g, 0.576 mmol) as white solid which was used in subsequent reactions without further purification. RP-HPLC (Table 1, Method b) Rt 1.97 min; m/z: (M+H)+ 263.

Workup

  1. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-9a53a018168b49389a0a67de38ba08a8
Source dataset
uspto-grants-2014_06
Patent number
US08754107B2

Reaction notes

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