tert-Butyl 4-(4-(((benzyloxy)carbonyl)amino)-3-methylphenyl)-5,6-dihydropyridine-1(2H)-carboxylate → Tert-butyl 4-(4-amino-3-methylphenyl)piperidine-1-carboxylate

HRID 2272441Notes

Reaction equation

HRID 2272441 reaction equation
C(OC([NH:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH:19]=2)=[CH:14][C:13]=1[CH3:31])=O)C1C=CC=CC=1>CO.[Pd]>[NH2:11][C:12]1[CH:17]=[CH:16][C:15]([CH:18]2[CH2:19][CH2:20][N:21]([C:24]([O:26][C:27]([CH3:29])([CH3:28])[CH3:30])=[O:25])[CH2:22][CH2:23]2)=[CH:14][C:13]=1[CH3:31]

Participants

4

Reactant 1

HCID 68283391tert-Butyl 4-(4-(((benzyloxy)carbonyl)amino)-3-methylphenyl)-5,6-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 68283578Tert-butyl 4-(4-amino-3-methylphenyl)piperidine-1-carboxylateYield 76.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of tert-butyl 4-(4-(((benzyloxy)carbonyl)amino)-3-methylphenyl)-5,6-dihydropyridine-1(2H)-carboxylate (I52) (798 mg, 2.49 mmol) and 10% Pd/C (250 mg) in MeOH (50 mL) was stirred under hydrogen (1 atm) for 16 hours at room temperature. The resulting mixture was filtered through celite, washing with MeOH, then the volatiles were removed by evaporation under reduced pressure to give the title compound (I53) (550 mg, 76%) as a purple/brown liquid; 1H NMR (400 MHz, CDCl3) δ 6.95 (d, J=6.7 Hz, 3H), 4.22 (s, 2H), 2.77 (s, 2H), 2.54 (s, 1H), 2.29 (s, 3H), 1.77 (d, J=12.7 Hz, 2H), 1.56 (dd, J=12.6, 3.7 Hz, 9H), 1.47 (s, 9H). LCMS Method C rt: 5.09 min; m/z 235.1 [M-tBu+2]+, 191.2 [M-Boc+2]+.

Workup

  1. filtrationThe resulting mixture was filtered through celite
  2. washwashing with MeOH
  3. customthe volatiles were removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-b266d18e9066422eba104dc73dc86502
Source dataset
uspto-grants-2015_09
Patent number
US09120761B2

Reaction notes

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