Nitrogen → Tert-butyl 1-(3-aminopyridin-4-yl)-3-methylpiperidin-3-ylcarbamate

HRID 69909Notes

Reaction equation

HRID 69909 reaction equation
N#N.[CH3:3][C:4]1([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH2:9][CH2:8][CH2:7][N:6]([C:10]2[CH:15]=[CH:14][N:13]=[CH:12][C:11]=2[N+:16]([O-])=O)[CH2:5]1>[Pd].CO>[NH2:16][C:11]1[CH:12]=[N:13][CH:14]=[CH:15][C:10]=1[N:6]1[CH2:7][CH2:8][CH2:9][C:4]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:3])[CH2:5]1

Participants

5

Reactant 2

HCID 947NitrogenHCID 69094616HCID 69094616, compound

Product 1

HCID 69094721Tert-butyl 1-(3-aminopyridin-4-yl)-3-methylpiperidin-3-ylcarbamate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

10% Palladium on carbon (0.1 eq) was added to a N2-flushed solution of tert-butyl 3-methyl-1-(3-nitropyridin-4-yl)piperidin-3-ylcarbamate (1 eq) in MeOH (0.2 M). The reaction was purged with H2 under atmospheric pressure for 16 h at it. The crude solids were filtered through a pad of Celite on a paper lined Buchner funnel, washed with EtOAc and MeOH, then concentrated in vacuo. The crude residue was dissolved in CH2Cl2, loaded onto a SiO2 column, and purified by flash chromatography (1:2 EtOAc in hexanes+5% MeOH) to give tert-butyl 1-(3-aminopyridin-4-yl)-3-methylpiperidin-3-ylcarbamate. LC/MS (m/z): 307.2 (MH+).

Workup

  1. customThe reaction was purged with H2 under atmospheric pressure for 16 h at it
  2. filtrationThe crude solids were filtered through a pad of Celite on a paper
  3. washwashed with EtOAc and MeOH
  4. concentrationconcentrated in vacuo
  5. dissolutionThe crude residue was dissolved in CH2Cl2
  6. custompurified by flash chromatography (1:2 EtOAc in hexanes+5% MeOH)

Sources & evidence

ORD record
ord-a0b132c82ca64477b0ad508f0a9c667e
Source dataset
uspto-grants-2014_09
Patent number
US08822497B2

Reaction notes

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