Diethyl Ether → 1-((2R,4R)-1-(6-(6-ethanesulfonyl-pyridin-3-yloxy)-2-pyridin-2-yl-3H-benzimidazol-5-yl)-4-hydroxy-pyrrolidin-2-yl)-ethanone

Participants

Reaction Conditions

Reaction Steps

0.360 ml of methyl lithium (1.0 M diethyl ether solution was added to a tetrahydrofuran (1 ml) solution of 20 mg of (2R,4R)-1-(6-(6-ethanesulfonyl-pyridin-3-yloxy)-2-pyridin-2-yl-3H-benzimidazol-5-yl)-4-hydroxy-pyrrolidin-2-carboxylic acid methoxy-methyl-amide obtained in (step 1), at −78° C. The reaction liquid was stirred at −78° C. for 1 hour, heated up to 0° C. and stirred for 1 hour. Aqueous saturated ammonium chloride solution was added to the reaction liquid, extracted with ethyl acetate, and dried with anhydrous magnesium sulfate. The solvent was evaporated away under reduced pressure, and the resulting residue was purified through partitioning thin-layer chromatography (Kieselgel™ 60F254, Art 5744 (by Merck), chloroform/methanol=10/1) to obtain the entitled compound as a pale yellow solid.

Provenance & Evidence