2-methylpropan-2-yl 4-[4-nitro-3-(propan-2-yloxy)phenyl]-3,6-dihydropyridine-1(2H)-carboxylate → Tert-butyl 4-(4-amino-3-isopropoxyphenyl)piperidine-1-carboxylate

HRID 518811Notes

Reaction equation

HRID 518811 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH2:11][CH2:12][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:14][CH:15]=2)=[CH:6][C:5]=1[O:23][CH:24]([CH3:26])[CH3:25])([O-])=O>CO.[Pd]>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[CH2:11][CH2:12][N:13]([C:16]([O:18][C:19]([CH3:20])([CH3:21])[CH3:22])=[O:17])[CH2:14][CH2:15]2)=[CH:6][C:5]=1[O:23][CH:24]([CH3:26])[CH3:25]

Participants

4

Reactant 1

HCID 866979812-methylpropan-2-yl 4-[4-nitro-3-(propan-2-yloxy)phenyl]-3,6-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 86697982Tert-butyl 4-(4-amino-3-isopropoxyphenyl)piperidine-1-carboxylateYield 95.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 2.76 g of 2-methylpropan-2-yl 4-[4-nitro-3-(propan-2-yloxy)phenyl]-3,6-dihydropyridine-1(2H)-carboxylate in 60 ml of methanol is hydrogenated on 300 mg of palladium-on-carbon (10%) at a pressure of 10 bar and at ambient temperature for 3 h. The catalyst is removed by filtration on Celite and the filtrate is evaporated to dryness so as to obtain 2.44 g of 2-methylpropan-2-yl 4-[4-amino-3-(propan-2-yloxy)phenyl]piperidine-1-carboxylate in the form of a pink powder.

Workup

  1. customThe catalyst is removed by filtration on Celite
  2. customthe filtrate is evaporated to dryness so as

Sources & evidence

ORD record
ord-aead87a2c643479a9b509530b3b7e199
Source dataset
uspto-grants-2015_08
Patent number
US09115140B2

Reaction notes

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