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40.1.1.2.1.2.1 Variation 1: Amination with Azidotrimethylsilane Followed by Reduction

DOI: 10.1055/sos-SD-040-00112

Butenschön, H.Science of Synthesis, (200940178.

The oxidative amination of allylic positions in some steroids has been reported.[‌74‌] Treatment of steroids such as 92 with azidotrimethylsilane and lead(IV) acetate stereospecifically affords allylic azides e.g., 93 in 4574% yield (Scheme 25). While subsequent hydrogenation or reduction with zinc results in nitrogen-free reaction products, the reduction with lithium aluminium hydride affords acetylated 7α-aminocholesterol 94.

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Meeeee Meeeeeee Meee (e) Meeee (%) Meeeeeee Meee (e) Meeee (%) ee (°M)
8 M 888 88 8.8 88 888 [‌88‌]
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8 M 88 88 8 88 888 [‌88‌]
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(8β,8α)-8-Meeeeeeeeeee-8-ee-8-ee Meeeeee (88); Meeeeee Meeeeeeee:[‌88‌]

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(8β,8α)-8-Meeeeeeeeeee-8-ee-8-ee Meeeeee (88):[‌88‌]

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Meeeeeee Meeeee ee Meeeeeeee Meeeeeeee (Meeee 8); Meeeeee Meeeeeeee:[‌88‌]

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