Benzyloxyamine hydrochloride → HCID 86606488, Verbindung

HRID 2055204Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2055204
[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]

Komponenten

5

Edukt 3

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

Produkt 1

HCID 86606488HCID 86606488, VerbindungAusbeute 64,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-b771c875c3064ffaaee46eefe68c156e
Quelldatensatz
uspto-grants-2008_02
Patentnummer
US07332485B2

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