Hydroxyamine hydrochloride → 1-[5-Hydroxy-3-(Hydroxymethyl)-2,3-Dihydro-1,4-Benzodioxin-6-yl]-1-Ethanone Oxime

HRID 720379

Reaktionsgleichung

Reaktionsgleichung von HRID 720379
Cl.[NH2:2][OH:3].C(O)C.N1C=CC=CC=1.[OH:13][C:14]1[C:23]2[O:22][C@@H:21]([CH2:24][OH:25])[CH2:20][O:19][C:18]=2[CH:17]=[CH:16][C:15]=1[C:26](=O)[CH3:27]>C(O)C>[OH:13][C:14]1[C:23]2[O:22][CH:21]([CH2:24][OH:25])[CH2:20][O:19][C:18]=2[CH:17]=[CH:16][C:15]=1[C:26](=[N:2][OH:3])[CH3:27]

Komponenten

5

Edukt 3

HCID 443297Hydroxyamine hydrochlorideHCID 21975839Pyridine ethanolHCID 690170061-[(3S)-5-hydroxy-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-1-Ethanone

Produkt 1

HCID 1363432661-[5-Hydroxy-3-(Hydroxymethyl)-2,3-Dihydro-1,4-Benzodioxin-6-yl]-1-Ethanone Oxime

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of hydroxylamine hydrochloride (2.38 g, 34.2 mmole) in 1:1 ethanol/pyridine (100 mL) was added to a solution of 1-[(3S)-5-hydroxy-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-1-ethanone (1.92 g, 8.57 mmole) in ethanol (200 mL). It was then heated to reflux under nitrogen for 5 hours. Upon cooling, the solvent was removed and replaced with ethyl acetate. The solution was then washed with water (200 mL) and with aqueous 2N HCl (100 mL), dried over magnesium sulfate, filtered and evaporated in vacuum to give 1.89 g (93%) of the (S)-enantiomer of the title compound as a gray solid, m.p. 162° C. MS (ESI) m/z 240 (M+H)+.

Aufarbeitung

  1. temperatureIt was then heated
  2. temperatureto reflux under nitrogen for 5 hours
  3. temperatureUpon cooling
  4. customthe solvent was removed
  5. washThe solution was then washed with water (200 mL) and with aqueous 2N HCl (100 mL)
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated in vacuum

Quellen und Nachweise

ORD-Eintrag
ord-09e507d23a114a3db9bc54d448c6f64f
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07135479B2

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