Methanol → HCID 68915996, compound

Participants

Reaction Steps

32 g Trimethyl phosphine was added over 2 hours to 19 g [3-((1R,3R)-3-azido-indan-1-yl)-5-chloro-indol-1-yl]-phosphonic acid diphenyl ester in 100 mL pyridine and 36 mL 9N ammonium hydroxide at room temperature. The reaction mixture was stirred over night at room temperature and concentrated in vacuo. Ethyl acetate and water were added. The mixture was made basic with aqueous NaOH and filtered. The organic phase was concentrated in vacuo and was dissolved in ethyl acetate again. The ethyl acetate solution was extracted with 2×250 mL 2N methanesulfonic acid. The aqueous phase was made basic with 9N NaOH to form a precipitate, which was subjected to flash chromatography (ethyl acetate, methanol, triethylamine, silica gel) to give 0.6 g (1R,3R)-3-(5-chloro-1H-indol-3-yl)-indan-1-ylamine. The ethyl acetate phase from above was concentrated in vacuo and was dissolved in 100 mL methanol and 10 mL 30% NaOMe in methanol was added. The reaction mixture was stirred 2 hours at room temperature, concentrated in vacuo and purified by flash chromatography (ethyl acetate, methanol, triethylamine, silica gel) to give further 0.45 g (1R,3R)-3-(5-chloro-1H-indol-3-yl)-indan-1-ylamine.

Provenance & Evidence