Peracetic Acid → 14-Hydroxymorphinone

HRID 1513318Notes

Reaction equation

HRID 1513318 reaction equation
[CH3:1][N:2]1[C@@H:18]2[CH2:19][C:7]3[CH:8]=[CH:9][C:10]([OH:22])=[C:11]4[O:12][C@H:13]5[C:14]([O:20]C)=[CH:15][CH:16]=[C:17]2[C@:5]5([C:6]=34)[CH2:4][CH2:3]1.C(OO)(=[O:25])C>CC(O)=O.O>[CH3:1][N:2]1[C@H:18]2[CH2:19][C:7]3[CH:8]=[CH:9][C:10]([OH:22])=[C:11]4[O:12][C@H:13]5[C:14]([CH:15]=[CH:16][C@:17]2([OH:25])[C@:5]5([C:6]=34)[CH2:4][CH2:3]1)=[O:20]

Participants

4

Reactant 2

HCID 6585Peracetic AcidHCID 5462306Oripavine

Product 1

HCID 7175141914-Hydroxymorphinone

Reagents, catalysts & solvents 1

HCID 21899381Acetic acid--water (1/1)Solvent

Conditions

Temperature
25 °C

Procedure

To a 200 mL flask, dried oripavine (10.00 g, 95% wt/wt %) was dissolved in HOAc/H2O (1:4, 100 mL) and cooled to 5° C. to 10° C. Peroxyacetic acid, CH3CO3H, (9.1 mL, 32% wt/wt %) was added over 3 minutes and the reaction mixture was stirred at 5° C. to 10° C. for 30 minutes. HPLC data showed that the reaction was completed. The reaction mixture was allowed to warm to 25° C. for 30 minutes. H2C2O4 (3.0 g) was added to the reaction mixture, and was stirred at room temperature for 30 minutes and then heated to 50° C. for 30 minutes. The solution was assayed by HPLC and >99% conversion was observed.

Workup

  1. temperaturecooled to 5° C. to 10° C
  2. stirringwas stirred at room temperature for 30 minutes
  3. temperatureheated to 50° C. for 30 minutes

Sources & evidence

ORD record
ord-bc1b1b5e10254519b47e9fa6f53c6ba0
Source dataset
uspto-grants-2012_07
Patent number
US08217175B2

Reaction notes

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