Reaktion #565201

ord-a7ed59d3536a4587ad159f665ffd92b1

Reaktionsgleichung

O
Water
C=CCN1CC[C@]23c4c5ccc(O)c4O[C@H]2C(=O)CC[C@@]3(O)[C@H]1C5.Cl
naloxone hydrochloride
Cl.NO
hydroxylamine hydrochloride
[Na+].[OH-]
NaOH
→
C=CCN1CC[C@]23c4c5ccc(O)c4O[C@H]2C(=NO)CC[C@@]3(O)[C@H]1C5
6-Oximino-17-ally-4,5 α-epoxy-3, 14-dihydroxymorphinan

Edukte

O
Water
C=CCN1CC[C@]23c4c5ccc(O)c4O[C@H]2C(=O)CC[C@@]3(O)[C@H]1C5.Cl
naloxone hydrochloride
Cl.NO
hydroxylamine hydrochloride
[Na+].[OH-]
NaOH

Reagenzien

Keine

Lösungsmittel

CO
MeOH

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Extraktionthe oxime extracted into CHCl3 (3×50 mL)
  2. 2
    TrocknenThe extract was dried (MgSO4)
  3. 3
    Sonstigethe solvent evaporated
  4. 4
    SonstigeThe residue obtained
  5. 5
    Sonstigewas recrystallized from CH2Cl2 -petroleum ether
  6. 6
    SonstigeIR: (KBr): No C=O absorption at 1717 cm-1

Vorschrift

A mixture of naloxone hydrochloride (1.085 g, 3 mmol) and hydroxylamine hydrochloride (0.28 g, 4 mmol) was taken up in 30 mL of MeOH containing 2.8 mL of 10% aqueous NaOH. The mixture was stirred at room temperature for 24 h. Water was added (100 mL), and the oxime extracted into CHCl3 (3×50 mL). The extract was dried (MgSO4), and the solvent evaporated. The residue obtained was recrystallized from CH2Cl2 -petroleum ether. Yield: 840 mg (81.8%); mp: 119 C. IR: (KBr): No C=O absorption at 1717 cm-1. 1H NMR (CDCl3) δ 4.98 (s,C5H); Rf: silica gel 60 in EtOAc--EtOH--NH4OH (100:1:1) 0.13. Anal. Calcd for: C19H22N2O4C, 66.65; H, 6.48; N, 8.18. Found: C, 66.70; H, 6.52; N, 8.08.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04889860uspto-grants-1989_12