Sodium borohydride → 4-(2'-Fluoro-4-biphenylyl)-4-hydroxy-butyric acid

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Reaction Steps

45.9 gm (0.169 mol) of 4-(2'-fluoro-4-biphenylyl)-4-oxo-butyric acid were dissolved in a solution of 11.2 gm of potassium hydroxide in 450 ml of water at 35° C. While stirring, a solution of 6.4 gm (0.169 mol) of sodium borohydride in water was added. After stirring for about 3 hours, the mixture was acidified and extracted with ethyl acetate. From the washed and dried organic phase, the cyclohexylamine salt was precipitated by addition of cyclohexylamine. Yield: 41 gm (65% of theory); m.p. 174°-175° C.; melting point of the free acid: 120°-122° C. (from benzene); melting point of the isobutylamine salt: 125°-127° C. (from isopropanol); melting point of the morpholine salt: 108°-110° C. (from isopropanol); melting point of the sodium salt: 222°-224° C. (from ethanol).

Provenance & Evidence