Ethanol → (S)-tert-butyl 3-((3-aminopyridin-4-yl)oxy)piperidine-1-carboxylate

HRID 524933Notes

Reaction equation

HRID 524933 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][CH:7]=[CH:8][C:9]=1[O:10][C@H:11]1[CH2:16][CH2:15][CH2:14][N:13]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:12]1)([O-])=O.CCO>CCOC(C)=O.[Pd]>[NH2:1][C:4]1[CH:5]=[N:6][CH:7]=[CH:8][C:9]=1[O:10][C@H:11]1[CH2:16][CH2:15][CH2:14][N:13]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:12]1

Participants

5

Reactant 2

HCID 702EthanolHCID 86720990tert-butyl(3S)-3-[(3-nitro-4-pyridyl)oxy]piperidine-1-carboxylate

Product 1

HCID 86720991(S)-tert-butyl 3-((3-aminopyridin-4-yl)oxy)piperidine-1-carboxylateYield 102.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Pd on C, (10%, wet, Degussa) (1 g, 0.9397 mmol) was added to a stirred solution of tert-butyl (3S)-3-[(3-nitro-4-pyridyl)oxy]piperidine-1-carboxylate (2.65 g, 8.196 mmol) in EtOAc (30 mL)/EtOH (15 mL). The reaction was placed under an atmosphere of hydrogen and stirred at ambient temperature for 16 hours. The catalyst was removed by filtration through a pad of celite and the filtrate concentrated in vacuo to give the sub-title compound as an off-white solid (2.46 g, >100% Yield). MS (2ES+) 587.3.

Workup

  1. customThe catalyst was removed by filtration through a pad of celite
  2. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-8b2bb26d32494b96a9a59da65df3c9f9
Source dataset
uspto-grants-2016_05
Patent number
US09340546B2

Reaction notes

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