Hydrochloric Acid → HCID 21107387, compound

Participants

Reaction Steps

m-Chloroperoxybenzoic acid (mCPBA) (50%, 0.44 g) was added portionwise over 10 minutes to a solution of 2-chloro-5-ethenyl-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)benzamide (Example 9a)) (0.42 g)), (S,S)-[N,N′-bis(3,5-di-tertbutylsalicylidene)-1,2-cyclohexanediaminato(2-)]manganese(III) chloride (44 mg) and N-methylmorpholine (0.74 g) in dichloromethane (10 mL) at −78° C. After stirring for 8 hours, a further portion of mCPBA (0.13 g) was added and the solution was left to warm slowly to room temperature over 16 hours. Sodium hydroxide (NaOH) (2M) was added, stirred for 1 hour and then methylamine (2M in methanol, 2 mL) was added. After stirring for 24 hours the reaction was concentrated, dichloromethane and water were added, the phases were separated and the aqueous was extracted with dichloromethane. The combined organic phases were dried over anhydrous sodium sulfate and concentrated. The resulting oil was purified by reverse phase HPLC (gradient 25–95% methanol in 1% aqueous trifluoroacetic acid). Further purification was performed by column chromatography (methanol/dichloromethane/ammonia (0.88) 1:20:0.5 to 15:100:0.5) gave an oil. Addition of excess 1M ethereal hydrogen chloride gave the titled compound as a white solid (158mg).

Provenance & Evidence