(3S)-(-)-3-(tert-Butoxycarbonylamino)pyrrolidine → (S)-tert-butyl 1-(6-cyano-9-((2-(trimethylsilyl)ethoxy)methyl)-9H-dipyrido[2,3-b;4',3'-d]pyrrol-4-yl)pyrrolidin-3-ylcarbamate

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-chloro-9-(2-trimethylsilanyl-ethoxymethyl)-9H-dipyrido[2,3-b;4′,3′-d]pyrrole-6-carbonitrile (590 mg, 1.6 mmol) and (S)-tert-butyl pyrrolidin-3-ylcarbamate (918 mg, 4.9 mmol) in N,N-dimethylacetamide (7.6 mL) was heated at 100° C. for 2 hours. The cooled reaction mixture was diluted with ethyl acetate (100 mL) and washed with water (40 mL). The organic layer was separated, dried over sodium sulfate, filtered, concentrated in vacuo, and purified by flash chromatography (silica, 12 g, ISCO, 0-90% ethyl acetate in heptane) to afford the title compound as a white solid, which was used in the next step without any further purification (530 mg, 63%).

Provenance & Evidence