Potassium Carbonate → HCID 54561569, compound

HRID 1683738Notes

Reaction equation

HRID 1683738 reaction equation
[CH:1](=[C:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C:9]1=[N:14][OH:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.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:15][N:14]=[C:9]2[CH2:10][CH2:11][CH2:12][CH2:13][C:8]2=[CH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:23]1)=[O:21])[CH3:18]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 189199HCID 189199, compoundHCID 70009171(R)-1-(2-bromoethyl)nipecotic acid ethyl ester hydrobromide

Product 1

HCID 54561569HCID 54561569, compoundYield 35.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of the above oxime (3.7 g, 18.4 mmol), (R)-1-(2-bromoethyl)-3-piperidinecarboxylic acid ethyl ester hydrobromide (7.0 g, 20.2 mmol, EP 374801), potassium carbonate (10.2 g, 73.5 mmol) and acetone (150 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 (200 g, heptane/ethyl acetate=3/2) to give 2.5 g of (R)-1-(2-(((2-(benzylidene)cyclohexylidene)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 (200 g, heptane/ethyl acetate=3/2)

Sources & evidence

ORD record
ord-6a0a6e53df27443294320ae09860f0a5
Source dataset
uspto-grants-1997_06
Patent number
US05639766

Reaction notes

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