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

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Reaction Conditions

Reaction Steps

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%).

Provenance & Evidence