Potassium Hydroxide → 1-(2-Aminophenyl)-2-cyclopropylcyclobutanol

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Reaction Steps

In a sulfonation flask, a mixture consisting of 3.35 g (0.0145 mol) N-[2-(2-cyclopropyl-1-hydroxycyclobutyl)phenyl]-formamide (prepared as described in Example 3), 1.3 g (0.02 mol) potassium hydroxide and 25 ml methanol was stirred at reflux temperature for 3 hours. Then the solvent was distilled off in a water jet vacuum and the residue taken up in 100 ml of ethyl acetate. The organic phase was washed three times with water and after drying with sodium sulphate the solvent was distilled off in a water jet vacuum. The raw material was purified by flash chromatography over silica gel (eluant: hexane/ethyl acetate 2:1). Yield: 2.4 g (80% of theory) of 1-(2-aminophenyl)-2-cyclopropylcyclobutanol in the form of a slightly brownish oil (1HNMR (CDCl3): 0.2-0.36 ppm/m/2H, 0.55 ppm/m/2H), 1.08 ppm/m/1H), 1.81 ppm/m/2H, 2.3-2.48 ppm/m/3H, 4.2 ppm (broad)/3H−NH2+OH), 6.6-6.72 ppm/m/2H, 7.05-7.15/m/2H− only one isomer obtained).).

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