97453-25-3Relevant articles and documents
Synthesis of Deuterium-Labelled 16α-Hydroxy-4-androstene-3,17-dione and 16α-hydroxydehydroepiandrosterone
Numazawa, Mitsuteru,Ogata, Mieko
, p. 865 - 868 (2007/10/02)
16α-Hydroxy-4-androstene-3,17-dione-d5 (4) and 3β,16α-hydroxy-5-androsten-17-one-d6 (10) were synthesized.Treatment of 16α-bromo-5-androstene-3,17-dione (2) with deuterium oxide and methanol-OD gave the 4-en-3-oxo derivative-d 3.The bromide 3 was converted into the 16α-hydroxy-d5 4 via controlled alkaline hydrolysis using sodium hydroxide-OD in deuterium oxide-pyridine. 3β-Hydroxy-5-androstene-17-one-d5 (8), which was obtained from 17,17-ethylenedioxy-5-androsten-3-one (5) via treatment with potassium tert-butoxide in tert-butanol-OD, followed by lithium aluminium tri-tert-butoxydeuteride reduction and then acid hydrolysis, was derivatized to the 16α-bromide 9 by treatment with cupric bromide.The bromide 9 was similarly hydrolyzed to yield the 16α-hydroxide-d6 10.Keywords - controlled alkaline hydrolysis; deuterium labelling; 16α-bromodehydroepiandrosterone-d5; 16α-bromoandrostenedione-d4; 16α-hydroxydehydroepiandrosterone-d6; 16α-hydroxyandrostenedione-d5.