Chlorotrimethylsilane → HCID 21465245, compound

Participants

Reaction Conditions

Reaction Steps

330 mg of 6-(1-isoquinolyloxy)-4-methoxymethyl-β-carboline-3-carboxylic acid isopropyl ester is mixed in 10 ml of toluene with 0.62 ml of triethylamine and 0.2 chlorotrimethylsilane and heated for 45 minutes to a bath temperature of 50°-60° C. After concentration by evaporation to about 6 ml, it is cooled to -78° C. under argon and 1.25 ml of a 1.2 molar diisobutyl aluminum hydride is instilled in hexane. After 30 minutes at -78° C., it is mixed with 3 ml of ethanol and 0.75 ml of 1N NaOH. It is mixed with ethyl acetate and very little water. The organic phase is separated and concentrated by evaporation without drying. The residue is mixed with hexane and yields 440 mg of 6-(1-isoquinolyloxy)-4-methoxymethyl-β-carboline-3-carbaldehyde. 254 mg of it is mixed in 2.5 ml of dimethylfuran with 67.5 mg of hydroxylamine hydrochloride and 69 mg of potassium hydroxide powder and allowed to stand for 16 hours at room temperature. The batch is poured on ice and the precipitate is suctioned off and rewashed with water. 133 mg of 6-(1-isoquinolyloxy-4-methoxymethyl-β-carboline-3-carbaldehyde oxime of melting point 215°-218° C. is obtained.

Provenance & Evidence