Ozone → 2-chloro-5,11-dihydro-11-ethyl-8-(2-hydroxyethyl)4methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one

Participants

Reaction Steps

A stream of O3 was introduced into a cold (−78° C.) solution of 2-chloro-5,11-dihydro-11-ethyl-4-methyl-8-(2-propenyl)-6H-dipyrido[3,2-b:2′,3′-e] [1,4]diazepin-6-one (8.04 g, 24.4 mmol) and Sudan III in CH2Cl2 (120 mL) and MeOH (120 mL). When the pink solution turned brown, O2 was bubbled through the solution for 10 min. NaBH4 (1.12 g, 29.4 mmol) was then added and the solution was allowed to warm to room temperature. After 30 min, an additional amount of NaBH4 (500 mg) was added. After 1 h, aqueous saturated NH4Cl was then added and the mixture stirred for 20 min. The solution was concentrated under reduced pressure and extracted with CH2Cl2 (3×). The combined organic extracts were washed with brine, dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (CHCl3:EtOH, 97:3) to give the title compound (6.01 g, 74% yield) as a white solid.

Provenance & Evidence