1-(Tert-butoxycarbonyl)-4-(4-phenylbutylidene)piperidine → 1-(Tert-butoxycarbonyl)-4-(4-phenylbutyl)piperidine

HRID 2095423Notes

Reaction equation

HRID 2095423 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](=[CH:14][CH2:15][CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[OH-].[OH-].[Pd+2]>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([CH2:14][CH2:15][CH2:16][CH2:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 593714671-(Tert-butoxycarbonyl)-4-(4-phenylbutylidene)piperidine

Product 1

HCID 538430051-(Tert-butoxycarbonyl)-4-(4-phenylbutyl)piperidine

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of 1-(tert-butoxycarbonyl)-4-(4-phenylbutylidene)piperidine (216 mg, 0.69 mmol) in MeOH (10 mL) was added 20% Pd(OH)2/C (50 mg). The mixture was warmed to reflux under a H2 atmosphere for 6 h. After filtration and concentration, 1-(tert-butoxycarbonyl)-4-(4-phenylbutyl)piperidine was obtained (202 mg, 92%) as a pale yellow oil, which was used in the following step without purification. 1H NMR (CDCl3, 400 MHz) δ 7.27 (m, 2H), 7.19 (m, 3H), 4.07 (d, 2H, J=12.0 Hz), 2.63 (m, 4H), 1.57 (m, 3H), 1.46 (s, 9H), 1.34 (m, 3H), 1.24 (m, 3H), 1.06 (m, 2H).

Workup

  1. temperatureThe mixture was warmed
  2. temperatureto reflux under a H2 atmosphere for 6 h
  3. filtrationAfter filtration and concentration

Sources & evidence

ORD record
ord-40b914ce444c49c1aba88a94781c8a25
Source dataset
uspto-grants-2013_05
Patent number
US08445684B2

Reaction notes

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