Sodium Bicarbonate → Oxycodone

HRID 508306Notes

Reaction equation

HRID 508306 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.C([O-])(O)=O.[Na+]>O>[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]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 5462350Oxycodone Hydrochloride

Product 1

HCID 5284603OxycodoneYield 98%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Oxycodone-hydrochloride (21.0 g, 59.7 mmol) was dissolved in water (250 mL). This solution was basified with saturated aqueous NaHCO3 (to pH 8-9) and extracted with DCM (3×250 mL). The combined organic layer was dried over Na2SO4 and filtered; removal of solvents under vacuum afforded Compound L in 98% yield (18.5 g, 58.8 mmol) as a white solid. LC-MS [M+H] 316.1 (C18H21NO4+H, calc: 316.2). Compound L was used directly in the next reaction without further purification.

Workup

  1. extractionextracted with DCM (3×250 mL)
  2. dry with materialThe combined organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. customremoval of solvents under vacuum

Sources & evidence

ORD record
ord-26f0ea54efd2460097d4006e9bfbdd4d
Source dataset
uspto-grants-2015_08
Patent number
US09095627B2

Reaction notes

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