Ammonium Hydroxide → Oxycodone

HRID 627005Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 627005
[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].C([O-])(=O)C.[OH-].[NH4+].S([O-])([O-])(=O)=O.[Na+].[Na+]>C(O)(C)C.C(Cl)(Cl)Cl>[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]

Komponenten

6

Edukt 3

HCID 14923Ammonium HydroxideHCID 24436Sodium SulfateHCID 86762802(4R,4aS,7aR,12bS)-4a-hydroxy-9-methoxy-3-methyl-2,4,5,6,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-one acetate

Produkt 1

HCID 5284603OxycodoneAusbeute 74,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3776IsopropanolLösungsmittelHCID 6212ChloroformLösungsmittel

Versuchsvorschrift

Oxycodone acetate solution was diluted with isopropanol (25 mL), cooled to 10° C. and neutralized at 10° C. to 5° C. with ammonium hydroxide (conc., ˜30 mL until pH˜9.5). Stirring continued for 10 minutes and precipitated solids were filtered off, washed on filter with water (20 mL, 2×50 mL, 10 mL) and dried on filter for 0.5 hours. The light gray wet material (22.29 g) was prepared. This material was dissolved in chloroform (150 mL), treated with sodium sulfate (anhydrous) for one hour. Solvent was removed in vacuum and gray powder was dried on rotary evaporator for one hour at 50° C. in the bath, providing oxycodone base (16.31 g, 51.72 mmol, 74.1% yield on ABUK sulfate). Impurity profile is shown in Table 8.

Aufarbeitung

  1. customprecipitated solids
  2. filtrationwere filtered off
  3. washwashed
  4. filtrationon filter with water (20 mL, 2×50 mL, 10 mL)
  5. customdried
  6. filtrationon filter for 0.5 hours
  7. customSolvent was removed in vacuum and gray powder
  8. customwas dried on rotary evaporator for one hour at 50° C. in the bath

Quellen und Nachweise

ORD-Eintrag
ord-3721b2d1a7ce4982ae4308050d20fb92
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09309257B2

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