Reaktion #67605

Reaktionsgleichung

N-(cyclobutylmethyl)-noroxymorphone

HCO2H

triethylamine

→

nalbuphine

Ausbeute 83.0%

Lösungsmittel

acetonitrile

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwere added
2. 2
   workup.STIRRINGThis reaction was stirred for 72 hours at room temperature
3. 3
   SonstigeThe reaction mixture was evaporated under reduced pressure
4. 4
   Sonstigeforming a thick brown oil
5. 5
   Sonstigefor 18 hours
6. 6
   Sonstigeyielded a brown solid
7. 7
   SonstigeThe solid was isolated by filtration, which
8. 8
   Waschenwas washed with acetonitrile (10 mL)
9. 9
   SonstigeDrying the solid

Vorschrift

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.

Quelle