HCID 68571590, compound → tert-Butyl 3-[4-ethyl-3-(3-methoxypropoxy)benzyloxy]-4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}piperidine-1-carboxylate

HRID 1712312Notes

Reaction equation

HRID 1712312 reaction equation
[CH3:1][O:2][C:3]1[CH:49]=[CH:48][CH:47]=[CH:46][C:4]=1[CH2:5][O:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([CH:17]2[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH:18]2[O:30][CH2:31][C:32]2[CH:37]=[CH:36][C:35]([CH:38]=[CH2:39])=[C:34]([O:40][CH2:41][CH2:42][CH2:43][O:44][CH3:45])[CH:33]=2)=[CH:13][CH:12]=1>C(N(CC)CC)C.CO.[Pd]>[CH2:38]([C:35]1[CH:36]=[CH:37][C:32]([CH2:31][O:30][CH:18]2[CH:17]([C:14]3[CH:13]=[CH:12][C:11]([O:10][CH2:9][CH2:8][CH2:7][O:6][CH2:5][C:4]4[CH:46]=[CH:47][CH:48]=[CH:49][C:3]=4[O:2][CH3:1])=[CH:16][CH:15]=3)[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19]2)=[CH:33][C:34]=1[O:40][CH2:41][CH2:42][CH2:43][O:44][CH3:45])[CH3:39]

Participants

5

Reactant 1

HCID 68571590HCID 68571590, compound

Product 1

HCID 68634511tert-Butyl 3-[4-ethyl-3-(3-methoxypropoxy)benzyloxy]-4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}piperidine-1-carboxylate

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8471TriethylamineSolvent

Procedure

The solution of 0.090 g of tert-butyl 4-{4-[3-(2-methoxybenyloxy)propoxy]phenyl}-3-[3-(3-methoxypropoxy)-4-vinylbenzyloxy]piperidine-1-carboxylate in 0.090 ml of triethylamine and 5.0 ml of methanol is hydrogenated in the presence of 10 mg of 10% Pd/C over 16 hours. The reaction mixture is clarified by filtration and the filtrate is concentrated by evaporation. The title compound is obtained as an orange oil from the residue by means of flash chromatography (SiO2 60F). Rf=0.23 (1:2 EtOAc-heptane); Rt=30.02 (II).

Workup

  1. filtrationThe reaction mixture is clarified by filtration
  2. concentrationthe filtrate is concentrated by evaporation

Sources & evidence

ORD record
ord-3f6df2d4cb6247dd98073114571061be
Source dataset
uspto-grants-2010_09
Patent number
US07790715B2

Reaction notes

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