Benzyloxyamine hydrochloride → 1-(Benzyloxyimino-methyl)-4,4-dimethyl-cyclohexanecarboxylic acid methyl ester

HRID 2055182Notes

Reaction equation

HRID 2055182 reaction equation
[CH3:1][O:2][C:3]([C:5]1([CH:13]=O)[CH2:10][CH2:9][C:8]([CH3:12])([CH3:11])[CH2:7][CH2:6]1)=[O:4].C([O-])(=O)C.[Na+].Cl.[CH2:21]([O:28][NH2:29])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CO>[CH3:1][O:2][C:3]([C:5]1([CH:13]=[N:29][O:28][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:6][CH2:7][C:8]([CH3:11])([CH3:12])[CH2:9][CH2:10]1)=[O:4]

Participants

5

Reactant 3

HCID 102312Benzyloxyamine hydrochlorideHCID 517045Sodium AcetateHCID 71416982Methyl 1-formyl-4,4-dimethylcyclohexane-1-carboxylate

Product 1

HCID 866064741-(Benzyloxyimino-methyl)-4,4-dimethyl-cyclohexanecarboxylic acid methyl esterYield 26%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of crude 1-formyl-4,4-dimethyl-cyclohexanecarboxylic acid methyl ester from Preparation 27 (22.9 mmol theoretical), sodium acetate (3.76 g, 45.8 mmol) and O-benzylhydroxylamine hydrochloride (7.32 g, 45.8 mmol) were stirred in methanol (100 mL) for 18 h. The methanol was removed in vacuo, water (100 mL) was added and the aqueous phase was extracted with EtOAc (50 mL×5). The combined organic extracts were dried (MgSO4) and were evaporated in vacuo. The residue was purified by flash column chromatography using an eluting system of hexane/EtOAc (99:1) to yield the title compound (1.83 g, 26%). MH+304.

Workup

  1. customThe methanol was removed in vacuo, water (100 mL)
  2. additionwas added
  3. extractionthe aqueous phase was extracted with EtOAc (50 mL×5)
  4. dry with materialThe combined organic extracts were dried (MgSO4)
  5. customwere evaporated in vacuo
  6. customThe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-76af3f0d1c544b77bed3257a36556b76
Source dataset
uspto-grants-2008_02
Patent number
US07332485B2

Reaction notes

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