Reaktion #933003

Reaktionsgleichung

water

oxymorphone

hydroxylamine hydrochloride

NaOH

→

6-Oximino-17-methyl-4,5α-epoxy-3,14-dihydroxymorphinan

Lösungsmittel

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted with 150 mL CHCl3 (3×50 mL)
2. 2
   ExtraktionThe CHCl3 extract
3. 3
   Trocknenwas dried (MgSO4)
4. 4
   Sonstigeevaporated
5. 5
   SonstigeThe residue was recrystallized from THF-petroleum ether yielding 600 mg (47.4%), mp 270°-71° C
6. 6
   SonstigeIR: (KBr): No C=O absorption at 1720 cm-1

Vorschrift

A solution of oxymorphone (1.2 g, 4 mmol) and hydroxylamine hydrochloride (0.35 g, 5 mmol) in 20 mL of methanol was treated with 2 mL of 10% aqueous NaOH and stirred at room temperature for 15 h. The reaction mixture was poured into water and extracted with 150 mL CHCl3 (3×50 mL). The CHCl3 extract was dried (MgSO4), and evaporated. The residue was recrystallized from THF-petroleum ether yielding 600 mg (47.4%), mp 270°-71° C. IR: (KBr): No C=O absorption at 1720 cm-1. H NMR (d6DMSO) δ 4.83 (s, C5H), Rf: silica gel EtOAc-EtOH-NH4OH (100:1:1) 0.18. Anal. Calcd for C17H20N2O4C, 64.54; H, 6.37; N, 8.86. Found C, 64.76; H, 6.5; N, 8.58.

Quelle