Water → Oxymorphone

HRID 2262668Notes

Reaction equation

HRID 2262668 reaction equation
O.[CH3:2][N:3]1[C@H:13]2[CH2:14][C:15]3[CH:20]=[CH:19][C:18]([OH:21])=[C:17]4[O:22][C@H:7]5[C:8]([CH:10]=[CH:11][C@:12]2([OH:23])[C@:6]5([C:16]=34)[CH2:5][CH2:4]1)=[O:9].[H][H]>[Pd].C(O)(=O)C>[CH3:2][N:3]1[C@@H:13]2[CH2:14][C:15]3=[CH:20][CH:19]=[C:18]([OH:21])[C:17]4[O:22][C@H:7]5[C:8]([CH2:10][CH2:11][C@:12]2([OH:23])[C@:6]5([C:16]=43)[CH2:5][CH2:4]1)=[O:9]

Participants

6

Reactant 3

HCID 962WaterHCID 7175141914-Hydroxymorphinone3×HCID 178418361HCID 178418361, compound2×

Product 1

HCID 5284604Oxymorphone

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
30 °C

Procedure

A hydrogenation vessel is charged with kg litre water and 0.73 kg acetic acid before adding 1 kg of 14-hydroxymorphinone prepared as in Example 1.1A and the mixture stirred until clear. 40 g of wet 10% Pd on carbon catalyst is added under a stream of nitrogen, and hydrogen supplied at 35-40 psi (2.41-2.76 bar). The temperature is maintained at 30±5° C. until hydrogen uptake stops, then the vessel is maintained at 35-40 psi (2.41-2.76 bar) and 30±5° C. for 3-4 hours. The reaction vessel is cooled to less than 25° C. and a sample subjected to HPLC to check for 14-hydroxymorphinone. If the 14-hydroxymorphinone area detected by HPLC is >0.1%, the hydrogenation is repeated.

Workup

  1. additionbefore adding
  2. temperatureThe reaction vessel is cooled to less than 25° C.

Sources & evidence

ORD record
ord-3ea81f9ceff148578563211c5d844345
Source dataset
uspto-grants-2010_12
Patent number
US07851482B2

Reaction notes

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