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

HRID 2055189Notes

Reaction equation

HRID 2055189 reaction equation
[CH3:1][O:2][C:3]([C:5]1([CH:12]=O)[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1)=[O:4].C([O-])(=O)C.[Na+].Cl.[CH2:20]([O:27][NH2:28])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CO>[CH3:1][O:2][C:3]([C:5]1([CH:12]=[N:28][O:27][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]1)=[O:4]

Participants

5

Reactant 3

HCID 102312Benzyloxyamine hydrochlorideHCID 517045Sodium AcetateHCID 71416981Methyl 1-formylcycloheptane-1-carboxylate

Product 1

HCID 866064791-(Benzyloxyimino-methyl)-cycloheptanecarboxylic acid methyl esterYield 51%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 1-formyl-cycloheptanecarboxylic acid methyl ester from Preparation 34 (35.6 mmol theoretical), sodium acetate (5.84 g, 72 mmol) and O-benzylhydroxylamine hydrochloride (11.36 g, 72 mmol) were stirred in methanol (71 mL) for 2 h. The methanol was removed in vacuo and the residue partitioned between water and EtOAc. The aqueous phase was extracted with EtOAc (50 mL×5). The combined organic extracts were dried (MgSO4) and were evaporated in vacuo. Purifiaction by flash column chromatography using an eluting sytem of hexanes/EtOAc (99:1) provided the title compound as a clear colorless oil (5.22 g, 51%). MH+290.

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×5)
  4. dry with materialThe combined organic extracts were dried (MgSO4)
  5. customwere evaporated in vacuo

Sources & evidence

ORD record
ord-6e862dc7709f4930b420426ce3b81598
Source dataset
uspto-grants-2008_02
Patent number
US07332485B2

Reaction notes

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