tert-butyl 4-(3-methoxy-4-nitrophenyl)-5,6-dihydropyridine-1(2H)-carboxylate → Tert-butyl 4-(4-amino-3-methoxyphenyl)piperidine-1-carboxylate

HRID 871850Notes

Reaction equation

HRID 871850 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:12]2[CH2:13][CH2:14][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:16][CH:17]=2)[CH:6]=[CH:7][C:8]=1[N+:9]([O-])=O>C(OCC)(=O)C.C(O)C.[Pd]>[NH2:9][C:8]1[CH:7]=[CH:6][C:5]([CH:12]2[CH2:13][CH2:14][N:15]([C:18]([O:20][C:21]([CH3:22])([CH3:23])[CH3:24])=[O:19])[CH2:16][CH2:17]2)=[CH:4][C:3]=1[O:2][CH3:1]

Participants

4

Reactant 1

HCID 56945492tert-butyl 4-(3-methoxy-4-nitrophenyl)-5,6-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 57416157Tert-butyl 4-(4-amino-3-methoxyphenyl)piperidine-1-carboxylateYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584252Ethanol ethylacetateSolvent

Procedure

4.27 g (12.77 mmol) of the product prepared in step 4.2 in 130 mL of an ethyl acetate/ethanol mixture (v/v=1/1) are placed in a hydrogenation autoclave, and 0.54 g of 10% palladium-on-charcoal is added, under an inert atmosphere. The mixture is stirred under a hydrogen pressure of 3 bar at room temperature. After filtration through thin glass fibre paper and evaporation under reduced pressure, 3.87 g of the expected product are obtained in the form of a pink solid, which is used as obtained in the following step. Yield=99%.

Workup

  1. additionis added, under an inert atmosphere
  2. filtrationAfter filtration
  3. customthrough thin glass fibre paper and evaporation under reduced pressure, 3.87 g of the expected product
  4. customare obtained in the form of a pink solid, which
  5. customas obtained in the following step

Sources & evidence

ORD record
ord-86718032c41e47d8a1067b176c3b6835
Source dataset
uspto-grants-2015_03
Patent number
US08975250B2

Reaction notes

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