Hydrogen Peroxide → Oxymorphone
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.OO.CC([OH:28])C>C(O)=O.[Pd]>[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]([CH2:15][CH2:16][C@:17]2([OH:28])[C@:5]5([C:6]=43)[CH2:4][CH2:3]1)=[O:20]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
Oripavine (64 g, 0.215 mol) was dissolved in formic acid (98-100%, 120 g) and hydrogen peroxide (30% in water, 24.5 g, 0.216 mol) added at 0° C. The mixture was pumped continuously at 2 ml/min through a 30 ml continuous flow reactor at 80° C. (15 min residence time). An analytical control after the continuous reactor showed less than 1% Oripavine remaining. The continuous stream was added directly to the hydrogenation autoclave that was precharged with 2-propanol (204 g), formic acid (98-100%, 64 g) and 5% Pd/C (7.6 g) and held at 100° C. under H2 (40 bar). The hydrogenation was stirred for 16 h. After the hydrogenation, the catalyst was filtered off and the crude mixture was either basified with NaOH to obtain the low impurity Oxymorphone base, or treated with HCl in 2-Propanol to give the Oxymorphone HCl. The yield was 82% for the base.
Workup
- customThe mixture was pumped continuously at 2 ml/min through a 30 ml continuous flow reactor at 80° C.
- custom(15 min residence time)
- additionThe continuous stream was added directly to the hydrogenation autoclave that
- customheld at 100° C. under H2 (40 bar)
- filtrationAfter the hydrogenation, the catalyst was filtered off
Sources & evidence
- ORD record
- ord-73543c32842a49d9939e7cada9b7a8ed
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08921557B2
Reaction notes
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