Ethanol → Ethyl 6-[1-(tert-butoxycarbonyl)piperidin-4-yl]pyridine-2-carboxylate

HRID 403199Notes

Reaction equation

HRID 403199 reaction equation
C([C:3]1([C:22]([O-:24])=[O:23])[NH:8][C:7]([C:9]2[CH2:10][CH2:11][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:13][CH:14]=2)=[CH:6][CH:5]=[CH:4]1)C.[CH2:25](O)[CH3:26]>[Pd]>[C:18]([O:17][C:15]([N:12]1[CH2:13][CH2:14][CH:9]([C:7]2[N:8]=[C:3]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH:4]=[CH:5][CH:6]=2)[CH2:10][CH2:11]1)=[O:16])([CH3:21])([CH3:19])[CH3:20]

Participants

4

Reactant 2

HCID 702EthanolHCID 866631211'-tert-Butyl 6-ethyl-3',6'-dihydro-2,4'-bipyridine-1',6(2'H)-dicarboxylate

Product 1

HCID 66686619Ethyl 6-[1-(tert-butoxycarbonyl)piperidin-4-yl]pyridine-2-carboxylate

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

1′-tert-Butyl 6-ethyl-3′,6′-dihydro-2,4′-bipyridine-1′,6(2′H)-dicarboxylate (31.5 g) is dissolved in ethanol (315 ml) and hydrogenated at room temperature under 1 bar of H2 in the presence of Pd/C (10%, 4.5 g) for 12 hours. Filtration and removal of the solvent under reduced pressure gives ethyl 6-[1-(tert-butoxycarbonyl)piperidin-4-yl]pyridine-2-carboxylate (30.5 g).

Workup

  1. filtrationFiltration and removal of the solvent under reduced pressure

Sources & evidence

ORD record
ord-cc2b1104dfe8471dae889bbb58f626fb
Source dataset
uspto-grants-2014_06
Patent number
US08748420B2

Reaction notes

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