title: Efficient syntheses of 17-β-amino steroids.
abstract: 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(PPh(3))(4) as catalyst.
authors.affiliation: Department of Chemistry, University of Waterloo, 200 University Ave. West, Waterloo, ON, Canada, N2L 3G1. s5taylor@sciborg.uwaterloo.ca
authors.forename: Scott D
authors.initials: SD
authors.lastname: Taylor
authors.forename: Jesse
authors.initials: J
authors.lastname: Harris
mesh_terms: D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013256:Steroids / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D013256:Steroids