Réaction #1702076

Équation de réaction

sodium bicarbonate

5-cyclopropyl-8-methoxy-2,3,5,6-tetrahydrobenzo[b][1,5]diazocin-4(1H)-one

magnesium trifluoromethanesulfonate

2-(phenoxymethyl)oxirane

→

desired compound

Rendement 65.0%

5-cyclopropyl-1-(2-hydroxy-3-phenoxypropyl)-8-methoxy-2,3,5,6-tetrahydrobenzo[b][1,5]diazocin-4(1H)-one

Rendement 65.0%

Solvants

acetonitrile

Conditions de réaction

Traitement

1. 1
   TempératureAfter cooling to room temperature
2. 2
   Extractionthe mixture was extracted with dichloromethane
3. 3
   FiltrationThe organic phases were filtered through a pad of sodium sulfate
4. 4
   Autrethe filtrate evaporated

Mode opératoire

To a mixture of 5-cyclopropyl-8-methoxy-2,3,5,6-tetrahydrobenzo[b][1,5]diazocin-4(1H)-one (50.0 mg, 0.203 mmol) from Example 1 and magnesium trifluoromethanesulfonate (32.7 mg, 0.102 mmol) in acetonitrile (1.5 ml) was added 2-(phenoxymethyl)oxirane (30.5 mg, 0.203 mmol) and the resulting mixture was stirred at 75° C. for 100 hours. After cooling to room temperature was added sodium bicarbonate (saturated aqueous) and the mixture was extracted with dichloromethane. The organic phases were filtered through a pad of sodium sulfate and the filtrate evaporated. Preparative thin layer chromatography (EtOAc/MeOH: 95/5) of the obtained residue, gave the desired compound as a brown oil (52 mg, 65%).

Source