Potassium Carbonate → (R)-1-(2-(((5-methyl-2-phenyl-2-hexen-1-ylidene)-amino)oxy)ethyl)-3-piperidinecarboxylic acid ethyl ester

HRID 975253Notes

Reaction equation

HRID 975253 reaction equation
[CH3:1][CH:2]([CH3:15])[CH2:3][CH:4]=[C:5]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH:6]=[N:7][OH:8].Br.[CH2:17]([O:19][C:20]([C@@H:22]1[CH2:27][CH2:26][CH2:25][N:24]([CH2:28][CH2:29]Br)[CH2:23]1)=[O:21])[CH3:18].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:17]([O:19][C:20]([C@@H:22]1[CH2:27][CH2:26][CH2:25][N:24]([CH2:28][CH2:29][O:8][N:7]=[CH:6][C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:4][CH2:3][CH:2]([CH3:15])[CH3:1])[CH2:23]1)=[O:21])[CH3:18]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 70009171(R)-1-(2-bromoethyl)nipecotic acid ethyl ester hydrobromideHCID 867504445-Methyl-2-phenyl-2-hexenal oxime

Product 1

HCID 54474992(R)-1-(2-(((5-methyl-2-phenyl-2-hexen-1-ylidene)-amino)oxy)ethyl)-3-piperidinecarboxylic acid ethyl esterYield 33.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of the above oxime (2.0 g, 10 mmol), (R)-1-(2-bromoethyl)-3-piperidinecarboxylic acid ethyl ester hydrobromide (3.4 g, 10 mmol), potassium carbonate (4.7 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, gradient 3/1 to 2/1) to give 1.3 g of (R)-1-(2-(((5-methyl-2-phenyl-2-hexen-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, gradient 3/1 to 2/1)

Sources & evidence

ORD record
ord-12606b80a9f64ab4b70d984749300cb8
Source dataset
uspto-grants-1997_03
Patent number
US05608069

Reaction notes

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