Water → 14-Hydroxymorphine-6-one

HRID 2275306Notes

Reaction equation

HRID 2275306 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:15].O>C(O)C.C(O)(CC)(C)C>[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]([CH:16]=[CH:17][C@:18]2([OH:21])[C@:5]5([C:6]=34)[CH2:4][CH2:3]1)=[O:15]

Participants

5

Reactant 2

HCID 962WaterHCID 5284604Oxymorphone

Product 1

HCID 1528625314-Hydroxymorphine-6-one

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 64052-Methyl-2-butanolSolvent

Conditions

Temperature
82.5 °C

Procedure

Crude oxymorphone, which contains residual water and, in some instances, can also contain residual ethanol, is dissolved in tert-amyl alcohol and the solution dried to remove water. This oxymorphone solution is then treated with excess allyl chloroformate (compound (102)) and sodium bicarbonate at 70-85° C. (Step 3). Once the reaction is complete (i.e., conversion of oxymorphone to the 3-allylcarbonate-N-allylcarbamate noroxymorphone (compound (109)), in which none, some, or all of the 14-OH can also be converted to a 14-allylcarbonate group (i.e., compound (110)), water and sodium carbonate are added and, in Step 4A, the mixture is heated to 80-85° C. for at least 15 hours to destroy excess allyl chloroformate and to hydrolyze the 3-carbonate moiety as well as any 14-carbonate groups that might be present, providing the 17-allylcarbamate derivative of noroxymorphone (compound (105)). The product, noroxymorphone-17-allylcarbamate, can be extracted into a suitable organic solvent which can be filtered, washed, and dried using normal work-up procedures. If desired, the product can be recovered by evaporation of that solvent.

Workup

  1. customthe solution dried
  2. customto remove water
  3. additionThis oxymorphone solution is then treated with excess allyl chloroformate (compound (102)) and sodium bicarbonate at 70-85° C. (Step 3)
  4. additionare added and, in Step 4A
  5. customto destroy excess allyl chloroformate

Sources & evidence

ORD record
ord-d1e715c0ac7342ffa9e95fe9c1f7d5f5
Source dataset
uspto-grants-2015_09
Patent number
US09127014B2

Reaction notes

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