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

HRID 1683744Notes

Reaction equation

HRID 1683744 reaction equation
[C:1]1([CH:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9](=[N:16][OH:17])[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br.[CH2:19]([O:21][C:22]([C@@H:24]1[CH2:29][CH2:28][CH2:27][N:26]([CH2:30][CH2:31]Br)[CH2:25]1)=[O:23])[CH3:20].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:19]([O:21][C:22]([C@@H:24]1[CH2:29][CH2:28][CH2:27][N:26]([CH2:30][CH2:31][O:17][N:16]=[C:9]2[C:10]3[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH2:8]2)[CH2:25]1)=[O:23])[CH3:20]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 70009171(R)-1-(2-bromoethyl)nipecotic acid ethyl ester hydrobromideHCID 731839393-Phenyl-1-indanone oxime

Product 1

HCID 53632844(R)-1-(2-(((3-phenyl-1-indanylidene)amino)oxy)ethyl)-3-piperidinecarboxylic acid ethyl esterYield 54.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of the above oxime (1.1 g, 5 mmol), (R)-1-(2-bromoethyl)-3-piperidinecarboxylic acid ethyl ester hydrobromide (1.7 g, 5 mmol, EP 374801), potassium carbonate (1.7 g, 13 mmol) and acetone (25 ml) was stirred at ambient temperature for 11 days. The mixture was filtered and the solvent evaporated in vacuo. The residue was purified by column chromatography on silica gel (100 g, heptane/ethyl acetate=1/1) to give 1.1 g of (R)-1-(2-(((3-phenyl-1-indanylidene)amino)oxy)ethyl)-3-piperidinecarboxylic acid ethyl ester as an oil.

Workup

  1. filtrationThe mixture was filtered
  2. customthe solvent evaporated in vacuo
  3. customThe residue was purified by column chromatography on silica gel (100 g, heptane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-ad6ea396043e4685b92236c6b46db79d
Source dataset
uspto-grants-1997_06
Patent number
US05639766

Reaction notes

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