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

HRID 478017Notes

Reaction equation

HRID 478017 reaction equation
[CH3:1][N:2]1[C@@H:19]2[CH2:20][C:7]3=[CH:8][CH:9]=[C:10]([OH:22])[C:11]4[O:12][C@H:13]5[C:14]([CH2:16][CH2:17][C@:18]2([OH:21])[C@:5]5([C:6]=43)[CH2:4][CH2:3]1)=O.Cl.[NH2:24][OH:25].[OH-].[Na+].O>CO>[N:24](=[C:14]1[CH2:16][CH2:17][C@:18]2([OH:21])[C@:5]34[CH2:4][CH2:3][N:2]([CH3:1])[C@@H:19]2[CH2:20][C:7]2[CH:8]=[CH:9][C:10]([OH:22])=[C:11]([O:12][C@@H:13]13)[C:6]4=2)[OH:25]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 5284604Oxymorphone

Product 1

HCID 867422906-Oximino-17-methyl-4,5alpha-epoxy-3,14-dihydroxymorphinan

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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. 1H NMR (d6DMSO) δ 4.83 (s, C5H), Rf: silica gel EtOAc-EtOH-NH40H (100:1:1) 0.18. Anal. Calcd for C17H20N2O4 :C, 64.54; H, 6.37; N, 8.86. Found C, 64.76; H, 6.5; N, 8.58.

Workup

  1. extractionextracted with 150 mL CHCl3 (3×50 mL)
  2. extractionThe CHCl3 extract
  3. dry with materialwas dried (MgSO4)
  4. customevaporated
  5. customThe residue was recrystallized from THF-petroleum ether yielding 600 mg (47.4%), mp 270-71 C
  6. customIR: (KBr): No C=O absorption at 1720 cm-1

Sources & evidence

ORD record
ord-861a8f79424c42aaa0bb924f35a243a6
Source dataset
uspto-grants-1989_12
Patent number
US04889860

Reaction notes

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