Dichloromethane → Oxycodone Hydrochloride

HRID 2369253Notes

Reaction equation

HRID 2369253 reaction equation
[CH3:1][N:2]1[C@@H:19]2[CH2:20][C:7]3[CH:8]=[CH:9][C:10]([O:22][CH3:23])=[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]=34)[CH2:4][CH2:3]1)=[O:15].[Cl:24]CCl>[Pd].C(O)(C)C>[CH3:1][N:2]1[C@@H:19]2[CH2:20][C:7]3[CH:8]=[CH:9][C:10]([O:22][CH3:23])=[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]=34)[CH2:4][CH2:3]1)=[O:15].[ClH:24]

Participants

5

Reactant 2

HCID 6344DichloromethaneHCID 5284603Oxycodone

Product 1

HCID 5462350Oxycodone Hydrochloride

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3776IsopropanolSolvent

Procedure

To a 250 mL hydrogenation bottle was charged 1.5 g (4.75 mmol, prepared via Rh catalyst rearrangement, 424 ppm 14-hydroxycodeinone) of oxycodone base, 6 mL of dichloromethane (DCM) and 2 mL of isopropanol (IPA). The mixture was agitated until a solution was obtained, then 0.15 g of 10% Pd/C was added. The mixture was hydrogenated with agitation at 35° C., 25 psi H2 and processed to isolated oxycodone HCl in portions after one and two days of hydrogenation.

Workup

  1. customwas obtained
  2. customwas hydrogenated with agitation at 35° C.

Sources & evidence

ORD record
ord-ff82a8d373404578831abbb6154cbb5e
Source dataset
uspto-grants-2014_04
Patent number
US08703950B2

Reaction notes

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