Potassium Carbonate → (R)-1-[2-[[2-(4-Fluoro-2-methylphenyl)-2-(2-methylphenyl)ethenyl]oxy]ethyl]-3-piperidine carboxylic acid ethyl ester

HRID 1460661Notes

Reaction equation

HRID 1460661 reaction equation
Br[CH2:2][CH2:3][O:4][CH:5]=[C:6]([C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:15]=1[CH3:21])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH3:13].Cl.[NH:23]1[CH2:33][CH2:32][CH2:31][CH:25]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH2:24]1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:29]([O:28][C:26]([C@@H:25]1[CH2:31][CH2:32][CH2:33][N:23]([CH2:2][CH2:3][O:4][CH:5]=[C:6]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:15]=2[CH3:21])[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[CH3:13])[CH2:24]1)=[O:27])[CH3:30]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 12896004Ethyl piperidine-3-carboxylate--hydrogen chloride (1/1)HCID 542963141-[2-(2-Bromoethoxy)-1-(2-methylphenyl)ethenyl]-4-fluoro-2-methylbenzene

Product 1

HCID 54574747(R)-1-[2-[[2-(4-Fluoro-2-methylphenyl)-2-(2-methylphenyl)ethenyl]oxy]ethyl]-3-piperidine carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1-[2-(2-Bromethoxy)-1-(2-methylphenyl)ethenyl]-4-fluoro-2-methylbenzene (1.15 g, 0.0033 mol), the (R)-enantiomer of ethyl nipecotate hydrochloride (see example 1) (1.92 g, 0.0099 mol) and dried potassium carbonate (2.28 g, 0.0165 mol) were stirred in acetone (100 ml) at reflux temperature for 54 h.

Workup

  1. temperatureat reflux temperature for 54 h.

Sources & evidence

ORD record
ord-e19f682f29964207af75a850c230b58b
Source dataset
uspto-grants-1991_12
Patent number
US05071859

Reaction notes

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