Formic Acid → Nalbuphine

HRID 1015685Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1015685
C(N(CC)CC)C.C(O)=O.[CH2:11]1[CH2:14][CH:13]([CH2:15][N:16]2[C@@H:26]3[CH2:27][C:28]4[CH:33]=[CH:32][C:31]([OH:34])=[C:30]5[O:35][C@H:20]6[C:21]([CH2:23][CH2:24][C@:25]3([OH:36])[C@:19]6([C:29]=45)[CH2:18][CH2:17]2)=[O:22])[CH2:12]1>C(#N)C.CC1C=CC(C(C)C)=CC=1.CC1C=CC(C(C)C)=CC=1.Cl[Ru]Cl.Cl[Ru]Cl>[CH:33]1[C:28]2[CH2:27][C@H:26]3[N:16]([CH2:15][CH:13]4[CH2:14][CH2:11][CH2:12]4)[CH2:17][CH2:18][C@:19]45[C@H:20]([C@@H:21]([OH:22])[CH2:23][CH2:24][C@@:25]34[OH:36])[O:35][C:30]([C:29]=25)=[C:31]([OH:34])[CH:32]=1

Komponenten

6

Edukt 3

HCID 284Formic AcidHCID 8471TriethylamineHCID 444650036-Ketonalbuphine

Produkt 1

HCID 5311304NalbuphineAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 10908223Dichloro(p-cymene)ruthenium(II) dimerKatalysatorHCID 6342AcetonitrileLösungsmittel2×

Versuchsvorschrift

Into a dried flask was added triethylamine (0.87 g, 8.6 mmol, 1.2 mL) and acetonitrile (5 mL). To this solution was added >96% HCO2H (0.99 g, 21.5 mmol, 0.81 mL). After stirring under nitrogen for 15 minutes, N-(cyclobutylmethyl)-noroxymorphone (1.02 g, 2.9 mmol) was added. Then, dichloro(p-cymene)ruthenium (II) dimer (10 mg, 0.0163 mmol) followed by (1S, 2S)-(+)-N-tosyl-diphenylethylene diamine (12 mg, 0.033 mmol) were added. This reaction was stirred for 72 hours at room temperature. HPLC analysis indicated that the reaction was complete. The reaction mixture was evaporated under reduced pressure forming a thick brown oil. Slurring the oil in acetonitrile (15 mL) for 18 hours yielded a brown solid. The solid was isolated by filtration, which was washed with acetonitrile (10 mL), Drying the solid yielded nalbuphine (0.85 g, 83% yield, 6-α: 99%) as a tan solid.

Aufarbeitung

  1. additionwere added
  2. stirringThis reaction was stirred for 72 hours at room temperature
  3. customThe reaction mixture was evaporated under reduced pressure
  4. customforming a thick brown oil
  5. customfor 18 hours
  6. customyielded a brown solid
  7. customThe solid was isolated by filtration, which
  8. washwas washed with acetonitrile (10 mL)
  9. customDrying the solid

Quellen und Nachweise

ORD-Eintrag
ord-b78dbb24a5dd4271bba23a0110f9f20d
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07985858B2

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