Hydrochloric Acid → 9-Acetyl-8-hydroxy-1,2-dihydro-6-(3-dimethylaminopropyl)-cyclopenta[c]carbazole-3-one

関与物質

反応条件

反応手順

A 0.5 M solution of BBr3 (16.5 mL, 5 eq.) was added dropwise under argon to a solution of compound 38 (0.658 g, 1.74 mmol) in CH2Cl2 (100 mL) cooled to −40° C. The mixture was kept for 10 min; then a cooling bath was removed and the mixture was heated to room temperature and kept for 1-2 h (TLC monitoring, eluent: CHCl3/NH3-MeOH, 9:1). The resulting mixture was poured in a mixture of aqueous NaHCO3 solution and CH2Cl2. The organic layer was separated; the aqueous one was extracted with CH2Cl2, dried over Na2SO4, evaporated, and dissolved in a mixture: CHCl3-MeOH-water, 40:9:1. The product was purified in a silica gel column with the use of the latter mixture as an eluent. Yield of Example 4: 0.258 g (41%). For the preparation of hydrochloride, the product isolated was dissolved in a mixture: CH2Cl2-MeOH; a solution of HCl in dioxane was added. The resulting mixture was evaporated to dryness; the residue was washed with ether.

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