Sodium Hydroxide → Oxymorphone

HRID 1513322Notes

Reaction equation

OS([O-])=O.[Na+].[OH-:6].[Na+].[CH3:8][N:9]1[C@@H:25]2[CH2:26][C:14]3[CH:15]=[CH:16][C:17]([OH:29])=[C:18]4[O:19][C@H:20]5[C:21]([O:27]C)=[CH:22][CH:23]=[C:24]2[C@:12]5([C:13]=34)[CH2:11][CH2:10]1.[OH-].[NH4+]>CC(O)=O>[CH3:8][N:9]1[C@@H:25]2[CH2:26][C:14]3=[CH:15][CH:16]=[C:17]([OH:29])[C:18]4[O:19][C@H:20]5[C:21]([CH2:22][CH2:23][C@:24]2([OH:6])[C@:12]5([C:13]=43)[CH2:11][CH2:10]1)=[O:27]

Participants

Conditions

Temperature: 38 °C

Procedure

To the above filtrate, NaHSO3 (0.1 g per g of oripavine) was added and nitrogen sweep was initiated. 50% Sodium Hydroxide, NaOH, (1.33 g per g of oripavine) was charged (pH=about 6.6). Temperature reached 35° C. during charging. The pH was adjusted with additional 50% NaOH (˜0.15 mL per g of oripavine) to 7.0. Note: The pH value would take 3 to 5 minutes to become steady. The pH adjustment was repeated until the pH change was within +/−0.2 over 5 minutes. The pH was adjusted to 6.6 to 7.0 with 50% NaOH or HOAc if necessary. The solution was heated and stirred at 38° C. (35° C. to 80° C.) for 2 hours to form a light brown solution (pH changed within +/−0.2). The solution was cooled to room temperature (20° C.). Concentrated ammonium hydroxide, c-NH4OH, (0.5 mL per g of oripavine) was added to form a precipitate (pH=9.0 to 10.0). The mixture was stirred at room temperature for 2 hours. The mixture was filtered, and the resulting solid was washed with water (3×1 mL per g of oripavine). The solid was dried under flowing air at room temperature for 1 hour to give product as a tan solid.

Workup

customreached 35° C.
customwas within +/−0.2 over 5 minutes
temperatureThe solution was heated
customto form a light brown solution (
temperatureThe solution was cooled to room temperature (20° C.)

Sources & evidence

ORD record: ord-3024379a53b5494ca0f96829f3f0f09f
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08217175B2

Reaction notes

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