tert-butyl 4-(4-amino-3-methoxy-phenyl)-3,6-dihydro-2H-pyridine-1-carboxylate → Tert-butyl 4-(4-amino-3-methoxyphenyl)piperidine-1-carboxylate

HRID 2272420Notes

Reaction equation

HRID 2272420 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH:9]=2)=[CH:4][C:3]=1[O:21][CH3:22]>CN(C=O)C.CCO.[Pd]>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:9][CH2:10][N:11]([C:14]([O:16][C:17]([CH3:18])([CH3:19])[CH3:20])=[O:15])[CH2:12][CH2:13]2)=[CH:4][C:3]=1[O:21][CH3:22]

Participants

5

Reactant 1

HCID 68455699tert-butyl 4-(4-amino-3-methoxy-phenyl)-3,6-dihydro-2H-pyridine-1-carboxylate

Product 1

HCID 57416157Tert-butyl 4-(4-amino-3-methoxyphenyl)piperidine-1-carboxylate

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Procedure

To a suspension of 10% Pd/C (0.068 g) in DMF (2 mL) under nitrogen was added a solution of tert-butyl 4-(4-amino-3-methoxyphenyl)-5,6-dihydropyridine-1(2H)-carboxylate (I33) (2.0 g, 6.5 mmol) in EtOH (50 mL) and the resulting suspension was stirred under an atmosphere of hydrogen at room temperature for 24 hours. The reaction mixture was filtered through celite, washing with ethyl acetate (100 mL). The filtrate was evaporated to dryness to give the title compound (I26) (1.42 g, 72%) as a light brown solid; 1H NMR (400 MHz, CDCl3) δ 6.66-6.58 (m, 3H), 4.21 (s, 2H), 3.76-3.66 (m, 4H), 2.53 (tt, J=12.1, 3.5 Hz, 1H), 1.84-1.75 (m, 2H), 1.55 (tdd, J=11.5, 6.4, 3.1 Hz, 1H), 1.47 (s, 9H).

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. washwashing with ethyl acetate (100 mL)
  3. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-564e4cecf8b94dc181fc0618175b0bf0
Source dataset
uspto-grants-2015_09
Patent number
US09120761B2

Reaction notes

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