Potassium Carbonate → HCID 54388268, compound

HRID 1683741Notes

Reaction equation

HRID 1683741 reaction equation
[C:1]1([CH:7]2[CH2:16][CH2:15][C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:8]2=[N:17][OH:18])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br.[CH2:20]([O:22][C:23]([C@@H:25]1[CH2:30][CH2:29][CH2:28][N:27]([CH2:31][CH2:32]Br)[CH2:26]1)=[O:24])[CH3:21].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:20]([O:22][C:23]([C@@H:25]1[CH2:30][CH2:29][CH2:28][N:27]([CH2:31][CH2:32][O:18][N:17]=[C:8]2[C:9]3[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH2:15][CH2:16][CH:7]2[C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:26]1)=[O:24])[CH3:21]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 70009171(R)-1-(2-bromoethyl)nipecotic acid ethyl ester hydrobromideHCID 71357281N-(2-Phenyl-3,4-dihydronaphthalen-1(2H)-ylidene)hydroxylamine

Product 1

HCID 54388268HCID 54388268, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of the above oxime (1.0 g, 4.2 mmol), (R)-1-(2-bromoethyl)-3-piperidinecarboxylic acid ethyl ester hydrobromide (2.2 g, 6.3 mmol, EP 374801), potassium carbonate (1.5 g, 11 mmol) and acetone (25 ml) was stirred at ambient temperature for 10 days. The mixture was filtered and the solvent evaporated in vacuo. The residue was purified by column chromatography on silica gel (150 g, heptane/ethyl acetate=7/3) to give 0.6 g of (R)-1-(2-(((2-phenyl-1,2,3,4-tetrahydro-1-naphthylidene)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 (150 g, heptane/ethyl acetate=7/3)

Sources & evidence

ORD record
ord-741bce7f311a4ba1a54bf9be877178bb
Source dataset
uspto-grants-1997_06
Patent number
US05639766

Reaction notes

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