Lithium borohydride → 5-(2-Hydroxyethyl)-N-{[6-(hydroxymethyl)-4-(trifluoromethyl)pyridin-2-yl]carbamoyl}-4-methylthiophene-2-sulfonamide

Participants

Reaction Steps

To a solution of 0.100 g methyl 6-[({[5-(2-acetoxyethyl)-4-methyl-2-thienyl]sulfonyl}carbamoyl)amino]-4-(trifluoromethyl)pyridine-2-carboxylate in 1.5 ml tetrahydrofuran was added 0.02 g lithiumborohydride and the mixture was stirred at room temperature for 3 h. The reaction mixture was partitioned between water and ethyl acetate. The phases were separated. The organic phase was washed with water. To he combined water phases was added 1 ml 10% citric acid and the mixture was extracted with ethyl acetate. The organic phase was washed with brine and evaporated to yield the title compound as white foam (containing acetoxy and hydroxyethyl ca 1:1) The mixture was dissolved in ca 2 ml methanol and ca 0.05 ml 28% sodium hydroxide and kept at room temperature for 5 h. The reaction mixture was partitioned between 10% citric acid and ethyl acetate. The phases were separated and the organic phase was washed with brine and evaporated to yield 0.049 g of the title compound as white foam. MS (ISN) M−H+=438.4

Provenance & Evidence