Ethyl Acetate → Tert-butyl 4-(4-amino-3-methoxyphenyl)piperidine-1-carboxylate

HRID 705742Notes

Reaction equation

HRID 705742 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:12]2[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH:13]=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

5

Reactant 2

HCID 8857Ethyl AcetateHCID 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 96%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

tert-Butyl 4-(3-methoxy-4-nitrophenyl)-5,6-dihydropyridine-1(2H)-carboxylate (I25) (5.609 g, 16.78 mmol) was dissolved in 1:1 ethanol:ethyl acetate (500 mL) and Pd/C (2.50 g) was added. The mixture was stirred vigorously under hydrogen for five hours then filtered through celite. The celite was washed with ethyl acetate (500 mL) and the combined filtrates evaporated to give the title compound (I26) (4.93 g, 96% yield) as an off-white solid; 1H NMR (400 MHz, CDCl3) δ 6.69-6.60 (m, 3H), 4.22 (s, 2H), 3.84 (s, 3H), 2.78 (t, J=12.4 Hz, 2H), 2.54 (tt, J=12.1, 3.5 Hz, 1H), 1.80 (d, J=13.1 Hz, 2H), 1.65-1.53 (m, 2H), 1.48 (s, 9H). LCMS Method C: rt 4.91 min; m/z 251.1 [M-tBu+2H]+, 207.2 [M-Boc+2H]+.

Workup

  1. filtrationthen filtered through celite
  2. washThe celite was washed with ethyl acetate (500 mL)
  3. customthe combined filtrates evaporated

Sources & evidence

ORD record
ord-3c8f38e9d9e84e45b80cebdb9c40d3ff
Source dataset
uspto-grants-2015_11
Patent number
US09174946B2

Reaction notes

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