Ethanolamine → tert-Butyl 4-{2-[3-(3-methoxypropyl)-1-methyl-1H-indol-5-ylmethyl]-3-methylbutyl}-2,2-dimethyloxazolidine-3-carboxylate

Participants

Reaction Steps

A solution of 2.80 g of tert-butyl 4-(2-{(2-methoxyacetoxy)-[3-(3-methoxypropyl)-1-methyl-1H-indol-5-yl]-methyl}-3-methylbutyl)-2,2-dimethyloxazolidine-3-carboxylate (diastereomer mixture) in 140 ml of ethanol is hydrogenated at 0° C. in the presence of 0.294 ml of ethanolamine and 3.34 g of 10% Pd/C over 3.5 hours. The reaction mixture is clarified by filtration and the filtrate is concentrated by evaporation. The title compound is obtained as a colourless oil from the residue by means of flash chromatography (SiO2 60F). Rf=0.48 (1:1 EtOAc-heptane). Rt=29.41 (gradient II).

Provenance & Evidence