Investigation on the synthesis of 25-hydroxycholesterol

•We report an new approach to the preparative synthesis of 25-hydroxycholesterol.•We examined the reaction of N-halosuccinimide with desmosterol.•We examined the reduction of bromohydrins with lithium aluminum hydride in THF.•We examined the reaction to the preparative synthesis of 24,25-monoepoxide by bromohydrins.•The parameters are optimized for yield of the final product.

A very efficient and environmentally benign method has been developed for the synthesis of 25-hydroxycholesterol. The reaction was performed in THF–water (4:1, v/v) using NBS as the brominating agent, followed by the easy reduction of C–Br with lithium aluminum hydride in THF, to yield the final product corresponding to a Markovnikov’s rule. Excellent yields and regioselectivity have been obtained.

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