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

HRID 2055172Notes

Reaction equation

HRID 2055172 reaction equation
[CH3:1][O:2][C:3]([C:5]1([CH:11]=O)[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1)=[O:4].C([O-])(=O)C.[Na+].Cl.[CH2:19]([O:26][NH2:27])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CO>[CH3:1][O:2][C:3]([C:5]1([CH:11]=[N:27][O:26][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]1)=[O:4]

Participants

5

Reactant 3

HCID 102312Benzyloxyamine hydrochlorideHCID 517045Sodium AcetateHCID 10866761Methyl 1-formylcyclohexane-1-carboxylate

Product 1

HCID 866064721-(Benzyloxyimino-methyl)-cyclohexanecarboxylic acid methyl esterYield 88%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 1-formyl-cyclohexanecarboxylic acid methyl ester (1.23 g, 7.23 mmol), sodium acetate (1.0 g, 14.5 mmol) and O-benzylhydroxylamine hydrochloride (2.3 g, 14.5 mmol) were stirred in methanol (40 mL) for 18 h. The methanol was removed in vacuo and the residue partitioned between water and EtOAc. The aqueous phase was extracted with EtOAc (50 mL×2). The combined organic extracts were dried (MgSO4) and were evaporated in vacuo to provide the title compound as a clear colorless liquid (1.75 g, 88%). MH+276.

Workup

  1. customThe methanol was removed in vacuo
  2. customthe residue partitioned between water and EtOAc
  3. extractionThe aqueous phase was extracted with EtOAc (50 mL×2)
  4. dry with materialThe combined organic extracts were dried (MgSO4)
  5. customwere evaporated in vacuo

Sources & evidence

ORD record
ord-05ed5baf925c4599b0b149fd91fc3b29
Source dataset
uspto-grants-2008_02
Patent number
US07332485B2

Reaction notes

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