Water → 6-Oximino-17-allyl-4,5alpha-epoxy-3,14-dihydroxymorphinan

HRID 845823Notes

Reaction equation

HRID 845823 reaction equation
[CH2:1]=[CH:2][CH2:3][N:4]1[C@@H:21]2[CH2:22][C:9]3[CH:10]=[CH:11][C:12]([OH:24])=[C:13]4[O:14][C@H:15]5[C:16]([CH2:18][CH2:19][C@:20]2([OH:23])[C@:7]5([C:8]=34)[CH2:6][CH2:5]1)=O.Cl.Cl.[NH2:27][OH:28].[OH-].[Na+].O>CO>[N:27](=[C:16]1[CH2:18][CH2:19][C@:20]2([OH:23])[C@:7]34[CH2:6][CH2:5][N:4]([CH2:3][CH:2]=[CH2:1])[C@@H:21]2[CH2:22][C:9]2[CH:10]=[CH:11][C:12]([OH:24])=[C:13]([O:14][C@@H:15]13)[C:8]4=2)[OH:28]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 5464092Naloxone Hydrochloride

Product 1

HCID 867422926-Oximino-17-allyl-4,5alpha-epoxy-3,14-dihydroxymorphinan

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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) δ4.98 (s,C5H); Rf: silica gel 60 in EtOAc-EtOH-NH4OH (100:1:1) 0.13. Anal. Calcd for: C19H22N2O4 : C, 66.65; H, 6.48; N, 8.18. Found: C, 66.70; H, 6.52; N, 8.08.

Workup

  1. extractionthe oxime extracted into CHCl3 (3×50 mL)
  2. dry with materialThe extract was dried (MgSO4)
  3. customthe solvent evaporated
  4. customThe residue obtained
  5. customwas recrystallized from CH2Cl2 -petroleum ether
  6. customIR: (KBr): No C=O absorption at 1717 cm-1

Sources & evidence

ORD record
ord-3f942aa9b1d34e9bb7af4014084fb8d0
Source dataset
uspto-grants-1988_07
Patent number
US04760069

Reaction notes

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