Ethyl Acetate → HCID 86590498, compound

HRID 1453982Notes

Reaction equation

HRID 1453982 reaction equation
[N+](=[CH2:3])=[N-].[F:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]2[CH2:17][CH:16]3[N:18]([CH3:19])[CH:13]([CH2:14][CH2:15]3)[CH:12]2[CH:20]=[N:21][OH:22])=[CH:7][CH:6]=1.C(OCC)(=O)C>CO.C(O)C>[CH3:3][O:22][N:21]=[CH:20][CH:12]1[CH:11]([C:8]2[CH:7]=[CH:6][C:5]([F:4])=[CH:10][CH:9]=2)[CH2:17][CH:16]2[N:18]([CH3:19])[CH:13]1[CH2:14][CH2:15]2

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 9550Diazomethane2×HCID 86590497HCID 86590497, compound

Product 1

HCID 86590498HCID 86590498, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

The carbaldehyde-oxime obtained above is converted to an alkyl oxime by treatment with a diazoalkane such as diazomethane. Thus 3-(4-fluoro-phenyl)-8-methyl-8-aza-bicyclo[3.2.1]octane-2-carbaldehyde oxime is dissolved in an appropriate alcohol such as methanol or ethanol or an organic solvent such as ethyl acetate and then this solution is cooled in an ice/water bath and then a solution of diazomethane. (excess 1.1-20 equivalents) is added. The reaction mixture should be stirred until the reaction is complete (TLC) and then the desired product isolated by solvent evaporation. The pure product is obtained by crystallization or flash column chromatography.

Workup

  1. addition(excess 1.1-20 equivalents) is added

Sources & evidence

ORD record
ord-0f452daea5804895a631741721964b57
Source dataset
uspto-grants-2009_01
Patent number
US07476740B2

Reaction notes

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