Science of Synthesis

Butenschön, H., Science of Synthesis, (2009) 40, 178.

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 45–74% 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.

‌Meeeee 88‌ Meeeeee Meeeeeeee ee e Meeeeeeeeee Meeeeeeeee[‌88‌]

Mee eeee eeeeeee, eee eeee eeeeeeee eeeeeeeee, eee eeeeeeee ee eeeeeee ee eeeeeeeee eeeeeeeeeeee eeeeeeeeeeee.[‌88‌] Mee eeeeeeeeeee ee 8,8-eeeeeeee-8,8-eeeeeeeeeeee-8,8-eeeeeee (MMM) ee ee eeeeeee eee eeeeeeeeeeeeeeeeeeee (Meeeee M) ee eeeeeeeee eeee (Meeeee M) ee eeeee eeeeee eeeeee eee eeeeeeeeeeeeee eeeeeeeeeeee ee ee eeeee eeeeeeeeeee ee eeeeeeee eeeeeeeee. Mee eeeee ee eeee eeeeeee eeeee eeeeeeeee eeeeeeeeeeeee ee eeee eee eeeeeeeeeeeee eeeeeeee eeeee. ‌Meeee 8‌ eeeeeeeeee eee eeeeeee.

‌Meeee 8‌ Meeeeeeee Meeeeeeeeeee Meeeeeeeeeee ee Meeeeeee Meeeeeeee[‌88‌]

Meeee	Meeeeeeee (M = M)	Meeeeeee Meeee (M = M8)			Meeeeeee Meeee Meeeeeeeeeeee (M = MM8•MMe)			Mee
		Meeeee	Meeeeeee Meee (e)	Meeee (%)	Meeeeeee Meee (e)	Meeee (%)	ee (°M)
8		M	888	88	8.8	88	888	[‌88‌]
8		M	88	88	8	88	888	[‌88‌]
8		M	888	88	8.8	88	888	[‌88‌]
8		M	888	88	8	88	888–888	[‌88‌]
8		M	88	88	8	88	888	[‌88‌]
8		M	888	88	8.88	88	888	[‌88‌]
8		M	888	88	8.8	88	888 (eee)	[‌88‌]

Meeeeeeeeeee Meeeeeeee

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

MMMMMMM: Meeeeee eeeeee eee eeeeee eeeeeeee eee eee eeeeeeeee eeeeeeeeeee. Mee eeeeeeeeee eeeeee ee eeeeeeeee ee e eeee eeee eeeee eeeeeeeeeee eeeeee eeeeeeeeeee eee eeeeeeeeee. Meeeeee ee eeeee eeeeee eeee eeeee eeeeeeeee eee eeeeee eeeee eee eeeeeeeee eeeeeeeee eeee.

MMMMMMM: Meeeeeeeeeeeeeeeeeee (eeeeeeeeeeeeee eeeee) ee eeeee ee eeeeeeeeee, eeee eeeeeeeeee, eee eeeeeeeee. Meee eee, eeee eeeeeee eee eeeeeee eee eeeee ee eeee e eeee ee eeeeeeeee eeee ee ee eeeeeee ee eeee ee e eeeee.

Mee eeeeeeee eee eeeeeeeee ee eeeee MM8Me8 [888 eM eee e Me(MMe)8]. M eeeee eeeee ee eeeeeee/MMMM8/Me(MMe)8 8:8:8 eee eeee. Meeeeee eee eeeeeeeeeee eeee eee eeeeee eeeeeeeee ee Me(M8)8 ee Me(MMe)M8, ee ee eeee eee eeee eeee 8 e ee Me(MMe)8 eeee. Mee eeeeeeeeee ee eee eeeeeeeeeee eee eeeeeeeee eeee eeeeeeee eeeeee eeeeeeeeeee.

Mee eeeeeeeeee eeeeee ee MMMM8 eee eeeee ee e eeee ee eee eeeeeee (8 eeee) ee MM8Me8 (888 eM) eee Me(MMe)8 (ee. 8.8 e). Mee eeee eee eeeeeee eeeee eeeeeeeee ee eeeeeeee ee 88°M eeeee eee ee eee eeeeeee eee eeeeeeee (8–88 e ee eeeeeeeee ee e eeeeee eee eeeeee e eeeee eeeeeeeeeee ee MeM eeee eeeeeeeeee). M8M eee eeeee, eee eee eeeeeeeeeee eee eeeeeeeee ee eeeeeeeeee eeeeeee e eeee eee eeeeeeeeee eeee MMM8. Meeee eeee eeeeeee eeee eee eeeeeee eeeee ee eeeeeeeeee eeee M8M. Meeee eeee ee MM8 ee MeMM eeee eeeeeee ee eeeeeeeeee eeee MeMMM8 eeee. Meeee eeeeeee eeee M8M, eee eeeeee ee eee eeeeeee eeeee (Me8MM8), eee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee, eee eee eeeeeeeee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, eeeeeeeee eeeee/eeeeeee 8:8, Me 8.88); eeeee: 88%; ee 888–888°M (MeMM); [α]M −888 (e 8.88).

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

MMMMMMM: Meeeeee eeeeee eee eeeeee eeeeeeee eee eee eeeeeeeee eeeeeeeeeee. Mee eeeeeeeeee eeeeee ee eeeeeeeee ee e eeee eeee eeeee eeeeeeeeeee eeeeee eeeeeeeeeee eee eeeeeeeeee.

MMMMMMM: Meeee eeeeeee eeeeeeee eeeeeee eeeeee eeeeeeeeee eeee e eeeeeee ee eeeeeeeeee, eee eee eeeeee ee eeeeeee ee eeeeeeee eeeeeeee.

M eeee ee eeeeeeeeeeeeee eeeee ‌88‌ (888 ee, 8.8 eeee) ee Me8M eee eeeee eeeeeeee ee e eeee ee MeMeM8 (888 ee) ee Me8M. Meeee eeeeeeeee eee eeeeeee eee 8 e, eee Me8M, M8M, eee MMe eeee eeeeeeeee eeeee, eee e eeeeeee (‌88‌•MMe) eeeeee, eeeee eee eeeeeeeeeeeeee (MMMe8/MeMM); eeeee: 888 ee (88%); ee 888–888°M. M eeeeeeeeee ee ‌88‌•MMe ee eeeeeee (MMMMMMM: eeeeeeeeee) eee 88% ee MeMM eee eeeeeee eeee ee eeeeeeee eeeeee ee eeee, eee eeee eee eeeeeee eeeee eee eeeee (M8MM8) eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee; eeeee: 88%; ee 888–888°M.

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

MMMMMMM: Meeeeeeeeeeeeeeeeeee (eeeeeeeeeeeeee eeeee) ee eeeee ee eeeeeeeeee, eeee eeeeeeeeee, eee eeeeeeeee. Meee eee, eeee eeeeeee eee eeeeeee eee eeeee ee eeee e eeee ee eeeeeeeee eeee ee ee eeeeeee ee eeee ee e eeeee.

MMMMMMM: Meeeeeeee eeee ee eeeeeeeee eeeeeeeee eee ee eeeeeeee eeeeeeeeeee ee eeeeeeeeeeee ee eeee eeeeee. Me ee e eeeeee eeeeeeee eeee eeeeeee ee eee eeeeeee eeeeeee eeeeee.

MMMMMMM: Meeeeee eeeeee eee eeeeee eeeeeeee eee eee eeeeeeeee eeeeeeeeeee. Mee eeeeeeeeee eeeeee ee eeeeeeeee ee e eeee eeee eeeee eeeeeeeeeee eeeeee eeeeeeeeeee eee eeeeeeeeee.

Meeeee M: MMM (888 ee, 8.8 eeee) eee eeeeeee eeeee ee e eeee-eeeeeee eeeeeee ee eee eeeeeeeeee (8.8 eeee), MMMe8 (8 eM), eee MMMM8 (8888 ee, 88.8 eeee). Meeeeeee eee eeeeeeeee ee 88°M eee 8–88 e. Mee eeeeeeeeee eee eeee eeeeee eeee 88% MeMMM8 eeee (888 eM) eee eee eeeeeee eee eeeeeeeee eeee Me8M (8 × 88 eM). Mee eeeeeeee eeeeeee eeeee eee eeeeee eeee M8M eeeee eeeeeee, eeeee (MeMM8), eee eeeeeeeee eeeeeeeeeeee ee eeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeeeee eeeeeee eee eeeee eeeeeeeeeeeeeee [eeeeee eee (8 e), eeeeeee/MeMMe 8:8 ee 8:8]. Mee eeeee eeeee (eeeeeeeeeeee eeee e eeeee eeeeee ee eeeeeeee eeeeeeee) eee ee eeee eee eee eeeeeeeee eeeeeee eeeeeeeeeeee. Mee eeeeee eee eeeeeee ee 8M MMM eeeeeeeeeeee. Meeeeeeeeeee eeee eeeeeee eeee eeeeeeee ee eeeeeeeeeee MMMM.

Meeeee M: MMM (888 ee, 8.8 eeee) eee eeeeeee eeeee ee e eeee-eeeeeee eeeeeee ee eee eeeeeeeeee (8.88 eeee) eee e MM8 eeee ee MMMe8 (88 eM, 8.8 eeee). Meeeeeee eee eeeeeeeee ee 88°M eee ee. 8 e. Mee eeeeee eee eeeeeeeee ee ee eeeeee M.

Meeeeeeee: M eeeeeee ee eee eeeee eeeeeeee eeeee (ee. 88 eeee) eee 8% Me/MeMM8 (888 ee) ee eeeee MeMM (88 eM) eee eeeeeee eeeee M8 (888 Meee) ee 88°M eee 8.8–8 e. Meeeeeeeee eeeeeee Meeeee eeeeeeee ee eeeeeee ee eee eeeeeeeee eeeeeee eeee Me8M eee eeeeeeeeeeeee eeeee eeeeeee eeeeeeee eeee eee eeeee eeeee. Meeee Me8M (88 eM) eee eeee eeeee, eee eee eeee eee eeeeeeeee eeee eeeee MMe eee 88 eee ee 8°M. Mee eeeeeeeeeee eee eeeeeeee, eeeeee eeee Me8M (8 × 8 eM), eee eeeee.

References

Meeeeee Meeeeeeeeee

• 8.Meeeee-Meee, (8888) M 88e8, 8888.