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

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Reaction Steps

Ozonised oxygen was introduced into a cold (−78° C.) solution of 2-chloro-5,11-dihydro-11-ethyl-5-methyl-8-(2-propenyl)-6H-dipyrido[3,2-b:2′,3′-e] [1,4]diazepin-6-one (13.4 g, 40.7 mmol) in MeOH (102 mL) and CH2Cl2 (102 mL) until complete disappearance of the alkene. Nitrogen was bubbled through the solution to remove excess O3. Solid NaBH4 (2.69 g, 71.1 mmol) was next added in small portions and the mixture was allowed to warm slowly to room temperature. After 1 h, aqueous saturated NH4Cl (150 mL) was added and the mixture stirred for 20 min. The organic solvents were removed under reduced pressure. Water (100 mL) was added to the aqueous solution. The solution was extracted with CHC13 (3×200 mL). The combined organic layers were dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (EtOAc:CHCl3, 4:1) to give the title compound (10.4 g, 77% yield).

Provenance & Evidence