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

HRID 1836969Notes

Reaction equation

HRID 1836969 reaction equation
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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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)+.

Workup

  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

Sources & evidence

ORD record
ord-4956449f0ac04d90adf10803c2031154
Source dataset
uspto-grants-2004_08
Patent number
US06780860B2

Reaction notes

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