Benzyloxyamine hydrochloride → HCID 86606488, compound

HRID 2055204Notes

Reaction equation

HRID 2055204 reaction equation
[CH3:1][O:2][C:3]([C:5]1([CH:13]=O)[CH2:8][CH:7]([CH2:9][CH2:10][CH2:11][CH3:12])[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][CH:7]([CH2:9][CH2:10][CH2:11][CH3:12])[CH2:8]1)=[O:4]

Participants

5

Reactant 3

HCID 102312Benzyloxyamine hydrochlorideHCID 517045Sodium AcetateHCID 71416977Methyl 3-butyl-1-formylcyclobutane-1-carboxylate

Product 1

HCID 86606488HCID 86606488, compoundYield 64.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 3-butyl-1-formyl-cyclobutanecarboxylic acid methyl ester (7.2 g, 36.7 mmol), sodium acetate (6.1 g, 73.4 mmol) and O-benzylhydroxylamine hydrochloride (11.9 g, 73.4 mmol) were stirred in methanol (90 mL) for 18 h. The methanol was removed in vacuo, water (100 mL) was added and the aqueous phase was extracted with EtOAc (75 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 (9:1) to yield the title compound as a clear colorless oil (7.23 g, 64%). MH+304.

Workup

  1. customThe methanol was removed in vacuo, water (100 mL)
  2. additionwas added
  3. extractionthe aqueous phase was extracted with EtOAc (75 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-b771c875c3064ffaaee46eefe68c156e
Source dataset
uspto-grants-2008_02
Patent number
US07332485B2

Reaction notes

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