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Potassium Carbonate → (R)-1-(2-(((2-phenyl-2-penten-1-ylidene)amino)oxy)ethyl)-3-piperidinecarboxylic acid ethyl ester

HRID 975251
Notes
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Reaction equation

HRID 975251 reaction equation
[C:1]1([C:7](=[CH:11][CH2:12][CH3:13])[CH:8]=[N:9][OH:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br.[CH2:15]([O:17][C:18]([C@@H:20]1[CH2:25][CH2:24][CH2:23][N:22]([CH2:26][CH2:27]Br)[CH2:21]1)=[O:19])[CH3:16].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:15]([O:17][C:18]([C@@H:20]1[CH2:25][CH2:24][CH2:23][N:22]([CH2:26][CH2:27][O:10][N:9]=[CH:8][C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:11][CH2:12][CH3:13])[CH2:21]1)=[O:19])[CH3:16]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 70009171(R)-1-(2-bromoethyl)nipecotic acid ethyl ester hydrobromideHCID 867504432-Phenyl-2-pentenal oxime

Product 1

HCID 54416283(R)-1-(2-(((2-phenyl-2-penten-1-ylidene)amino)oxy)ethyl)-3-piperidinecarboxylic acid ethyl esterYield 52.7%

Reagents, catalysts & solvents 1

HCID 180
Acetone
Solvent

Procedure

A mixture of the above oxime (2.0 g, 11 mmol), (R)-1-(2-bromoethyl)-3-piperidinecarboxylic acid ethyl ester hydrobromide (3.94 g, 11 mmol), potassium carbonate (4.73 g, 34 mmol) and acetone (25 ml) was stirred at room temperature for 4 days. The mixture was filtered and the solvent was evaporated from the filtrate in vacuo. The residue was purified by column chromatography on silica gel (75 g, cyclohexane/ethyl acetate 3/1) to give 2.08 g of (R)-1-(2-(((2-phenyl-2-penten-1-ylidene)amino)oxy)ethyl)-3-piperidinecarboxylic acid ethyl ester.

Workup

  1. filtrationThe mixture was filtered
  2. customthe solvent was evaporated from the filtrate in vacuo
  3. customThe residue was purified by column chromatography on silica gel (75 g, cyclohexane/ethyl acetate 3/1)

Sources & evidence

ORD record
ord-9c42a732ca604681bd202081a36a32bc
Source dataset
uspto-grants-1997_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05608069

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes