Potassium Carbonate → HCID 54217124, compound

HRID 975258Notes

Reaction equation

HRID 975258 reaction equation
[C:1]1([CH2:7][C:8](=[N:16][OH:17])[CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=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:8]([CH2:9][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:25]1)=[O:23])[CH3:20]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 745181,3-Diphenylacetone oximeHCID 70009171(R)-1-(2-bromoethyl)nipecotic acid ethyl ester hydrobromide

Product 1

HCID 54217124HCID 54217124, compoundYield 33.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of the above oxime (3.0 g, 13 mmol), (R)-1-(2-bromoethyl)-3-piperidinecarboxylic acid ethyl ester hydrobromide (4.6 g, 13 mmol), potassium carbonate (5.4 g, 39 mmol) and acetone (40 ml) was stirred at room temperature for 3 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 (50 g, cyclohexane/ethyl acetate 3/1) to give 1.8 g of (R)-1-(2-(((1,3-diphenylpropan-2-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 (50 g, cyclohexane/ethyl acetate 3/1)

Sources & evidence

ORD record
ord-08327dac90fb4447bd4aa5fe370eae03
Source dataset
uspto-grants-1997_03
Patent number
US05608069

Reaction notes

Loading…