tert-Butyl 4-((2-methoxy-5-nitrobenzyloxy)methyl)-4-phenylpiperidine-1-carboxylate → tert-Butyl 4-((5-amino-2-methoxybenzyloxy)methyl)-4-phenylpiperidine-1-carboxylate

HRID 391415Notes

Reaction equation

HRID 391415 reaction equation
[CH3:1][O:2][C:3]1[CH:30]=[CH:29][C:28]([N+:31]([O-])=O)=[CH:27][C:4]=1[CH2:5][O:6][CH2:7][C:8]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]1>CO.[Pd]>[NH2:31][C:28]1[CH:29]=[CH:30][C:3]([O:2][CH3:1])=[C:4]([CH:27]=1)[CH2:5][O:6][CH2:7][C:8]1([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]1

Participants

4

Reactant 1

HCID 58993459tert-Butyl 4-((2-methoxy-5-nitrobenzyloxy)methyl)-4-phenylpiperidine-1-carboxylate

Product 1

HCID 58993700tert-Butyl 4-((5-amino-2-methoxybenzyloxy)methyl)-4-phenylpiperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

tert-Butyl 4-((2-methoxy-5-nitrobenzyloxy)methyl)-4-phenylpiperidine-1-carboxylate (110 mg, 0.24 mmol) in methanol (3 mL) was flushed with nitrogen, and treated with palladium (10% on charcoal, 11.0 mg). The flask was flushed with hydrogen and allowed to stir under an atmosphere of hydrogen overnight. The reaction was flushed with nitrogen, filtered through celite, and concentrated to afford 96.0 mg (94%). 1H-NMR (CDCl3, 500 MHz) δ 7.33-7.38 (m, 4H), 7.22-7.25 (m, 1H), 6.62 (d, J=8.5 Hz, 1H), 6.51 (dd, J=5.8, 2.7 Hz, 1H), 6.29 (d, J=2.8 Hz, 1H), 4.37 (s, 2H), 3.70-3.74 (m, 2H), 3.43 (s, 3H), 3.42 (s, 2H), 3.03-3.07 (m, 2H), 2.15-2.18 (m, 2H), 1.88-1.93 (m, 2H), 1.43 (s, 9H). Mass spec.: 427.25 (MH)+.

Workup

  1. customThe flask was flushed with hydrogen
  2. customThe reaction was flushed with nitrogen
  3. filtrationfiltered through celite
  4. concentrationconcentrated
  5. customto afford 96.0 mg (94%)

Sources & evidence

ORD record
ord-079eb10618f74450b6b559fe1c3d0996
Source dataset
uspto-grants-2013_02
Patent number
US08383821B2

Reaction notes

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