[6-(1H-Tetrazol-1-yl)pyridine-3-yl]acetic acid → (3R)-3-methyl-6-[2-(4-{[6-(1H-tetrazol-1-yl)pyridin-3-yl]acetyl}piperazin-1-yl)ethyl]-3,4-dihydro-1H-isochromen-1-one

Participants

Reaction Steps

(3R)-3-methyl-6-[2-(4-{[6-(1H-tetrazol-1-yl)pyridin-3-yl]acetyl}piperazin-1-yl)ethyl]-3,4-dihydro-1H-isochromen-1-one and (3S)-3-methyl-6-[2-(4-{[6-(1H-tetrazol-1-yl)pyridin-3-yl]acetyl}piperazin-1-yl)ethyl]-3,4-dihydro-1H-isochromen-1-one 3-Methyl-6-[2-(4-{[6-(1H-tetrazol-1-yl)pyridin-3-yl]acetyl}piperazin-1-yl)ethyl]-3,4-dihydro-1H-isochromen-1-one was synthesized according to the procedure described for 3-methyl-6-[2-(3-methyl-4-{[4-(1H-tetrazol-1-yl)phenyl]acetyl}piperazin-1-yl)ethyl]-3,4-dihydro-1H-isochromen-1-one, utilizing [6-(1H-tetrazol-1-yl)pyridin-3-yl]acetic acid and 3-methyl-6-[2-(piperazin-1-yl)ethyl]-3,4-dihydro-1H-isochromen-1-one hydrochloride. LC-MS (IE, m/z): 462 [M+1]+. Separation of the two enantiomers was achieved by chiral preparative HPLC using a Chiralcel OD column eluting with 75% EtOH/Heptane to afford (3R)-3-methyl-6-[2-(4-{[6-(1H-tetrazol-1-yl)pyridin-3-yl]acetyl}piperazin-1-yl)ethyl]-3,4-dihydro-1H-isochromen-1-one and (3S)-3-methyl-6-[2-(4-{[6-(1H-tetrazol-1-yl)pyridin-3-yl]acetyl}piperazin-1-yl)ethyl]-3,4-dihydro-1H-isochromen-1-one both having LC-MS (IE, m/z): 462 [M+1]+.

Provenance & Evidence