Reaction #2446113

ord-de247159f21a44bdb1e41c8f39f2c63c

Reaction equation

COc1ccc2c3c1O[C@H]1C(=O)CC[C@@]4(O)[C@@H](C2)N(C)CC[C@]314.Cl
Oxycodone hydrochloride
O=C([O-])O.[Na+]
NaHCO3
→
COc1ccc2c3c1O[C@H]1C(=O)CC[C@@]4(O)[C@@H](C2)N(C)CC[C@]314
Compound L
Yield 98.0%
COc1ccc2c3c1O[C@H]1C(=O)CC[C@@]4(O)[C@@H](C2)N(C)CC[C@]314
Oxycodone
Yield 98.0%

Reactants

COc1ccc2c3c1O[C@H]1C(=O)CC[C@@]4(O)[C@@H](C2)N(C)CC[C@]314.Cl
Oxycodone hydrochloride
O=C([O-])O.[Na+]
NaHCO3

Reagents

None

Solvents

O
water

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Extractionextracted with DCM (3×250 mL)
  2. 2
    DryingThe combined organic layer was dried over Na2SO4
  3. 3
    Filtrationfiltered
  4. 4
    Otherremoval of solvents under vacuum

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.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08685916B2uspto-grants-2014_04