HCID 58458732, compound → HCID 178424242, compound

Participants

Reaction Steps

A solution of (RS)-8-chloro-5-methyl-1-(4-o-tolyl-cyclohex-3-enyl)-5,6-dihydro-4H-2,3,5,10b-tetraaza-benzo[e]azulene (0.10 g, 0.25 mmol) in acetic acid (2.5 ml) was purged with argon. After addition of platinum(IV) oxide (0.017 g, 0.075 mmol) the reaction vessel was filled with hydrogen. The reaction mixture was stirred under an atmosphere of hydrogen (1 bar) at room temperature for 48 h. The catalyst was removed by filtration over Decalite®. The filtrate was partitioned between ethyl acetate and aqueous 2 M sodium carbonate solution. The organic layer was collected. The aqueous layer was extracted with one portion of ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate and concentrated to dryness. Consecutive purification by flash column chromatography over aminopropyl modified silica gel with n-heptane/ethyl acetate as eluent and HPLC using a Chiralpac® AD column with n-heptane/2-propanol as eluent gave cis-8-chloro-5-methyl-1-(4-o-tolyl-cyclohexyl)-5,6-dihydro-4H-2,3,5,10b-tetraaza-benzo[e]azulene as white solid in 20% yield, trans-8-chloro-5-methyl-1-(4-o-tolyl-cyclohexyl)-5,6-dihydro-4H-2,3,5,10b-tetraaza-benzo[e]azulene as white solid in 11% yield and cis-5-methyl-1-(4-o-tolyl-cyclohexyl)-5,6-dihydro-4H-2,3,5,10b-tetraaza-benzo[e]azulene as off-white solid in 8% yield.

Provenance & Evidence