Tert-butyl 3-{2-[2-(2-acetylaminoethyl)-5-fluorophenoxy]ethoxy}-4-(4-benzyloxyphenyl)piperidine-1-carboxylate → HCID 68504580, compound

HRID 1176527Notes

Reaction equation

HRID 1176527 reaction equation
[C:1]([NH:4][CH2:5][CH2:6][C:7]1[CH:43]=[CH:42][C:41]([F:44])=[CH:40][C:8]=1[O:9][CH2:10][CH2:11][O:12][CH:13]1[CH:18]([C:19]2[CH:24]=[CH:23][C:22]([O:25]CC3C=CC=CC=3)=[CH:21][CH:20]=2)[CH2:17][CH2:16][N:15]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:14]1)(=[O:3])[CH3:2]>C(OCC)(=O)C.[Pd]>[C:1]([NH:4][CH2:5][CH2:6][C:7]1[CH:43]=[CH:42][C:41]([F:44])=[CH:40][C:8]=1[O:9][CH2:10][CH2:11][O:12][CH:13]1[CH:18]([C:19]2[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=2)[CH2:17][CH2:16][N:15]([C:33]([O:35][C:36]([CH3:37])([CH3:38])[CH3:39])=[O:34])[CH2:14]1)(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 68499818Tert-butyl 3-{2-[2-(2-acetylaminoethyl)-5-fluorophenoxy]ethoxy}-4-(4-benzyloxyphenyl)piperidine-1-carboxylate

Product 1

HCID 68504580HCID 68504580, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 5.8 g of tert-butyl 3-{2-[2-(2-acetylaminoethyl)-5-fluorophenoxy]ethoxy}-4-(4-benzyloxyphenyl)piperidine-1-carboxylate in 200 ml of ethyl acetate is hydrogenated at room temperature in the presence of 2.03 g of 10% Pd/C over 15 hours. The reaction mixture is clarified by filtration and the filtrate is concentrated by evaporation. The title compound is obtained as a white solid from the residue by means of flash chromatography (SiO2 60F). Rf=0.29 (EtOAc); Rt=4.30.

Workup

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

Sources & evidence

ORD record
ord-506bce2d77b844dcb8d5a01262873e6c
Source dataset
uspto-grants-2010_11
Patent number
US07842688B2

Reaction notes

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