Tetrahydrofuran → 6-benzyloxy-4-methoxymethyl-9-{2-[N-methyl-N-(2-phenylethyl)-amino]-2-oxoethyl}-9H-pyrido[3,4-b]indole-3-carboxylic acid-(1-methylethyl)-ester

Participants

Reaction Steps

998 mg of 6-benzyloxy-4-methoxymethyl-9H-pyrido[3,4-b]indole-3-carboxylic acid-1-methylethyl-ester (2.4 mmol) is introduced into 10 ml of dry tetrahydrofuran and deprotonated at 0° C. with 72 mg of sodium hydride (80% suspension in oil) (2.4 mmol). Then, it is stirred for 20 minutes at room temperature, mixed with 630 mg of 2-[N-methyl-N-(2-phenylethyl)-amino]-2-bromoacetamide (2.4 mmol)--dissolved in 10 ml of tetrahydrofuran--stirred for another 5 hours at room temperature, filtered on diatomaceous earth, and then the solvent is drawn off in a vacuum. The crude product that is obtained is recrystallized from dichloromethane/diethyl ether, and 1.22 g of 6-benzyloxy-4-methoxymethyl-9-{2-[N-methyl-N-(2-phenylethyl)amino]-2-oxoethyl}-9H-pyrido-[3,4-b]indole-3-carboxylic acid-(1-methyl-ethyl)-ester is obtained.

Provenance & Evidence