1,1-Dimethylethyl 3′,6′-dihydro[3,4′-bipyridine]-1′(2′H)-carboxylate → tert-Butyl 4-(pyridin-3-yl)piperidine-1-carboxylate

HRID 643574Notes

Reaction equation

HRID 643574 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH2:8][CH2:9][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:11][CH:12]=2)[CH:2]=1>C(O)C.[OH-].[OH-].[Pd+2]>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]2[CH2:8][CH2:9][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:11][CH2:12]2)[CH:2]=1

Participants

4

Reactant 1

HCID 589134081,1-Dimethylethyl 3′,6′-dihydro[3,4′-bipyridine]-1′(2′H)-carboxylate

Product 1

HCID 22061323tert-Butyl 4-(pyridin-3-yl)piperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

The tert-Butyl 3′,6′-dihydro-3,4′-bipyridine-1′(2′H)-carboxylate prepared in Step A (1.14 g, 4.38 mmol) was dissolved in 20 mL of ethanol and added to a flask containing palladium hydroxide on carbon powder (20% Pd). The reaction mixture was subjected to 50 psi of H2 (g) for 6.5 h with vigorous shaking. The reaction was then filtered and concentrated under reduced pressure. Purification by flash column chromatography (silica gel, 0-1% MeOH/EtOAc gradient eluent) afforded tert-butyl 4-pyridin-3-ylpiperidine-1-carboxylate. ESI-MS calc. for C15H22N2O2: 262.37, found 263 (M+H).

Workup

  1. additionadded to a flask
  2. filtrationThe reaction was then filtered
  3. concentrationconcentrated under reduced pressure
  4. customPurification by flash column chromatography (silica gel, 0-1% MeOH/EtOAc gradient eluent)

Sources & evidence

ORD record
ord-e3e804b48b174153be08ece85adbba8b
Source dataset
uspto-grants-2010_04
Patent number
US07700591B2

Reaction notes

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