Ammonium formate → Methyl 2-((1r,4r)-4-(4-(5-aminopyridin-2-yl)phenyl)cyclohexyl)acetate

HRID 1404252Notes

Reaction equation

HRID 1404252 reaction equation
[CH3:1][O:2][C:3](=[O:26])[CH2:4][CH:5]1[CH2:10][CH2:9][CH:8]([C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][C:20]([N+:23]([O-])=O)=[CH:19][N:18]=3)=[CH:13][CH:12]=2)[CH2:7][CH2:6]1.C([O-])=O.[NH4+]>[Pd].CCO>[CH3:1][O:2][C:3](=[O:26])[CH2:4][CH:5]1[CH2:10][CH2:9][CH:8]([C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][C:20]([NH2:23])=[CH:19][N:18]=3)=[CH:13][CH:12]=2)[CH2:7][CH2:6]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 66615867{4-[4-(5-Nitropyridin-2-yl)-phenyl]-cyclohexyl}-acetic acid methyl ester

Product 1

HCID 66615773Methyl 2-((1r,4r)-4-(4-(5-aminopyridin-2-yl)phenyl)cyclohexyl)acetate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of {4-[4-(5-Nitro-pyridin-2-yl)-phenyl]-cyclohexyl}-acetic acid methyl ester (1.4 g, 4.0 mmol) in 20 Ml EtOH was added Pd/C (0.4 g) followed by ammonium formate (2 g). The reaction mixture was heated to reflux for 4 h, then cooled to room temperature and filtered through Celite. Removal of solvent in vacuo afforded the title compound: 1H NMR (400 MHz, DMSO-d6) δ ppm 1.08-1.20 (m, 2 H) 1.43-1.54 (m, 1 H) 1.48 (dd, J=12.57, 2.46 Hz, 2H) 1.81 (d, J=11.75 Hz, 6 H) 2.26 (d, J=6.69 Hz, 2 H) 3.61 (s, 3 H) 6.98 (dd, J=8.59, 2.78 Hz, 1 H) 7.24 (d, J=8.34 Hz, 2 H) 7.57 (d, J=8.59 Hz, 1 H) 7.81 (d, J=8.34 Hz, 2 H) 8.00 (d, J=2.65 Hz, 1 H); (M+H)+ 325.2.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 4 h
  3. filtrationfiltered through Celite
  4. customRemoval of solvent in vacuo

Sources & evidence

ORD record
ord-b09e59ef63934114aaec862f008db67f
Source dataset
uspto-grants-2014_12
Patent number
US08912208B2

Reaction notes

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