Triphenylphosphine → HCID 67235237, compound

Participants

Reaction Steps

A solution of triphenylphosphine (19.4 g, 74.1 mmol) and DIAD (14.05 mL, 74.1 mmol) in THF (700 mL) is cooled to 0° C. and stirred for 10 min. Diethyl 1H-indole-2,6-dicarboxylate (15.47 g, 59.3 mmol) is added and reaction mixture is stirred for another 10 min. tert-Butyl 4-{[(tert-butoxycarbonyl)amino]methyl}-4-(hydroxymethyl)piperidine-1-carboxylate (17 g, 49.4 mmol) is added and the reaction mixture is stirred for 48 h at room temperature. The mixture is partitioned between water and ethyl acetate. and the organic layer is separated. The aqueous layer is extracted with ethyl acetate (2×200 mL). The combined organic layers are dried (Na2SO4), and concentrated. The residue is purified by flash column chromatography using 15% EtOAc in petroleum ether to afford the title compound (17 g, 32%) as a dark brown oil.

Provenance & Evidence