Dimethylformamide diethylacetal → HCID 14372947, compound

Participants

Reaction Steps

At 100° C., 500 mg of 3-acetyl-6-benzyloxy-4-methoxymethyl-β-carboline is stirred overnight in 5 ml of N,N-dimethylformamide diethylacetal. After concentration by evaporation, the mixture, without further purification, is taken up in 20 ml of absolute ethanol, combined with 600 mg of hydroxylamine-O-sulfonic acid in 5 ml of methanol, and stirred for 5 hours at room temperature. After neutralization with triethylamine, the reaction mixture is stirred overnight, introduced into water, and extracted with ethyl acetate; the organic phase is dried over magnesium sulfate and concentrated under vacuum. After chromatography over silica gel with acetone:triethylamine in a ratio of 10:1 as the eluent, 130 mg of 6-benzyloxy-4-methoxymethyl-3-(5-isoxazolyl)-β-carboline is obtained, melting point 125°-126° C.

Provenance & Evidence