Ammonium formate → HCID 86697966, compound

HRID 518797Notes

Reaction equation

HRID 518797 reaction equation
[CH2:1]([CH:3]1[N:8]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:7][CH2:6][C:5]([C:16]2[CH:21]=[CH:20][C:19]([N+:22]([O-])=O)=[C:18]([O:25][CH:26]([CH3:28])[CH3:27])[CH:17]=2)=[CH:4]1)[CH3:2].C([O-])=O.[NH4+]>[Pd].CO>[NH2:22][C:19]1[CH:20]=[CH:21][C:16]([CH:5]2[CH2:6][CH2:7][N:8]([C:9]([O:11][C:12]([CH3:13])([CH3:15])[CH3:14])=[O:10])[CH:3]([CH2:1][CH3:2])[CH2:4]2)=[CH:17][C:18]=1[O:25][CH:26]([CH3:27])[CH3:28]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 866979671(2H)-Pyridinecarboxylic acid, 2-ethyl-5,6-dihydro-4-[3-(1-methylethoxy)-4-nitrophenyl]-, 1,1-dimethylethyl ester

Product 1

HCID 86697966HCID 86697966, compoundYield 84.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

In a microwave tube, 470 mg of 2-methylpropan-2-yl 6-ethyl-4-[4-nitro-3-(propan-2-yloxy)phenyl]-3,6-dihydropyridine-1(2H)-carboxylate are introduced into 20 ml of methanol. 456 mg of ammonium formate and 385 mg of Pd/C (10%) are added. The reaction medium is microwave-heated at 80° C. for 5 minutes. The mixture is filtered on Clarcel and the Clarcel is rinsed with methanol. The filtrate is concentrated under reduced pressure. The residue is taken up with 30 ml of ethyl acetate and 3 ml of water. The organic phase is dried over magnesium sulfate, filtered and concentrated under reduced pressure, so as to obtain 370 mg of 2-methylpropan-2-yl 4-[4-amino-3-(propan-2-yloxy)phenyl]-2-ethylpiperidine-1-carboxylate in the form of a colourless oil.

Workup

  1. filtrationThe mixture is filtered on Clarcel
  2. washthe Clarcel is rinsed with methanol
  3. concentrationThe filtrate is concentrated under reduced pressure
  4. dry with materialThe organic phase is dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7c2a7b161f584461ab7f8245616cce84
Source dataset
uspto-grants-2015_08
Patent number
US09115140B2

Reaction notes

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