2-Propanol, 2-methyl-, lithium salt (1:1) → Rivaroxaban

Participants

Reaction Conditions

Reaction Steps

Under an atmosphere of nitrogen a suspension of 1.00 g of toluene-4-sulfonic acid (S)-3-[(5-chloro-thiophene-2-carbonyl)-amino]-2-[4-(3-oxo-morpholin-4-yl)-phenylcarbamoyloxy]-propyl ester (MW=608.09; 1 eq.) in 25 mL tetrahydrofuran was cooled to 0° C. At this temperature 1.6 mL of a 1M solution of lithium t-butoxide in tetrahydrofuran were added dropwise. After stirring at this temperature for 1 hour the resulting slurry was filtered. The cake was rinsed with 14 mL of tetrahydrofuran and 14 mL of water. The wet product was dried at 30° C. in vacuo to yield 0.63 g (MW=435.89; 1.013 eq.) of the title compound (88.5% of theory).

Provenance & Evidence