Morphine → Dihydromorphine

HRID 2185871Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2185871
[CH:1]1[C:17]2[CH2:16][C@H:15]3[N:18]([CH2:20][CH2:21][C@@:7]45[C@H:14]3[CH:13]=[CH:12][C@H:10]([OH:11])[C@@H:8]4[O:9][C:5]([C:6]=25)=[C:3]([OH:4])[CH:2]=1)[CH3:19].C(Cl)(Cl)Cl.CO>C(O)C>[CH3:19][N:18]1[C@@H:15]2[CH2:16][C:17]3[CH:1]=[CH:2][C:3]([OH:4])=[C:5]4[O:9][C@H:8]5[C@@H:10]([OH:11])[CH2:12][CH2:13][C@@H:14]2[C@:7]5([C:6]=34)[CH2:21][CH2:20]1

Komponenten

4

Edukt 2

HCID 5288826MorphineHCID 21584188Chloroform methanol

Produkt 1

HCID 5359421Dihydromorphine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To morphine free base (3 am, 10.5 mmol.) dissolved in absoTute ethanol (150 ml) palladium-on-activated carbon (5˜o) (1 am., 50 p.s.i.) was added. Reduction was carried out overnight (12-14 hours), in a Parr hydrogenator at ambient temperature. After confirmation of the quantitative conversion to 7,8-dihydromorphine by TLC, the ethanolic solution was filtered over Celite. The organic solvent ethanol was removed by rotary evaporation at reduced pressure, to afford 2.93 am. (97.2%) of dibydromorphine as an off-white glassy solid, homogeneous by TLC (CHCl3:MeOH (9:1), Rf=0.2). Elemental Analysis Calcd. for C17H21NO3:C, 71.08; H, 7.32; N, 4.88. Found: C, 71.11; H, 7.34; N, 4.91.

Aufarbeitung

  1. additionwas added
  2. custom(12-14 hours)
  3. customat ambient temperature
  4. filtrationAfter confirmation of the quantitative conversion to 7,8-dihydromorphine by TLC, the ethanolic solution was filtered over Celite
  5. customThe organic solvent ethanol was removed by rotary evaporation at reduced pressure
  6. customto afford 2.93

Quellen und Nachweise

ORD-Eintrag
ord-daeb21f2dacf4d66bf42d68acb75b9cb
Quelldatensatz
uspto-grants-2002_06
Patentnummer
US06403602B1

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