2640-80-4Relevant academic research and scientific papers
Efficient syntheses of 17-β-amino steroids
Taylor, Scott D.,Harris, Jesse
experimental part, p. 1098 - 1102 (2011/08/22)
17β-Amino steroids such as 17β-amino-1,3,5(10)-estratrien-3-ol (1), 17β-amino-5α-androstan-3β-ol (2) and, 17β-amino- 3β-hydroxyandrost-5-ene (3) have been widely used as a key intermediates in the synthesis of a variety of biologically active steroid derivatives though concise, high yielding syntheses of these compounds has yet to be reported. 17β-Amino-1,3,5(10)-estratrien-3-ol (1) and 17β-amino-5α- androstan-3β-ol (2) were prepared in high yield by reductive amination of estrone and epiandrosterone using benzylamine and sodium triacetoxyborohydride followed by catalytic hydrogenolysis of the resulting 17β-benzylamino derivatives. Attempts to prepare 17β-amino-3β-hydroxyandrost-5-ene (3) from dehydroepiandosterone using a similar approach resulted in partial reduction of the double bond. 17β-Amino-3β-hydroxyandrost-5-ene (3) was ultimately obtained in high yield by reductive amination of dehydroepiandosterone using allylamine and sodium triacetoxyborohydride followed by removal of the allyl group from the resulting 17β-allylamino derivative with dimethylbarbituric acid and Pd(PPh3)4 as catalyst.
Steroids, LIII: New Routes to Aminosteroids [1]
Szendi,Dombi,Vincze
, p. 1189 - 1196 (2007/10/03)
Steroid ketoximes were reduced with sodium tetrahydroborate in the presence of nickel chloride or molybdenum trioxide. These processes yielded 17α- and 20α- aminosteroids (1c-5c) in higher yields than common reduction methods.
