Sodium borohydride → HCID 11539185, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 1.62 g of the 2-(4-tert-butylphenyl)-5-dimethylaminomethyl-3-(4-methanesulfonylphenyl)-cyclopent-2-enone, hydrochloride obtained according to Example 15 in 15 ml methanol was combined in portions with 0.40 g of sodium borohydride with stirring at a temperature of 20° C. Once addition was complete, the resultant reaction mixture was stirred for a further three hours and completely evaporated under reduced pressure. The residue was redissolved in 50 ml of distilled water and adjusted to a pH value of 11 with addition of potassium carbonate. Extraction was then performed three times with 20 ml portions of ethyl acetate and the combined extracts were washed with saturated sodium chloride solution, dried over sodium sulfate and evaporated under reduced pressure. The resultant residue was purified by column chromatography on silica gel 60 (0.040–0.063 mm; E. Merck, Darmstadt, Germany) with a mixture of methanol and ethyl acetate in the ratio of 3:1 as eluent. 0.75 g of 2-(4-tert-butylphenyl)-5-dimethylaminomethyl-3-(4-methanesulfonylphenyl)-cyclopent-2-enol were obtained in the form of a colourless oil. This oil was redissolved in 25 ml of ethyl acetate and combined dropwise with stirring with 2 ml of a solution of hydrogen chloride in diethyl ether (5 wt. % HCl). A crystalline solid was obtained, which was isolated by suction filtration, washed with diethyl ether and dried under reduced pressure. 0.73 g of 2-(4-tert-butylphenyl)-5-dimethylaminomethyl-3-(4-methanesulfonylphenyl)-cyclopent-2-enol, hydrochloride (corresponding to 44.8% of theoretical) were obtained in the form of colourless crystals with a melting point of 223 to 224° C.

Provenance & Evidence