Synthesis of 21-amino-5-pregnene-3,20-dione bisethylene ketal.
21-Amino-5-pregnene-3,20-dione bisethylene ketal was obtained in good yield by lithium aluminum hydride reduction of 21-azido-5-pregnene-3,20-dione bisethylene ketal. The azido bisethylene ketal was synthesized by the sequence: deoxycorticosterone leads to deoxycorticosterone 21-p-toluene-sulfanate leads to 21-azidoprogesterone leads to 21-azido-5-pregnene-3, 20-dione bisethylene ketal. The structure of the title compound was confirmed by its conversion to the known 21-acetylaminoprogesterone. 21-Amino-5-pregnene-3,20-dione bisethylene ketal is a stable aminosteroid which is a useful intermediate for the synthesis of C-21 nitrogen derivatives of progesterone.
D002855:Chromatography, Thin Layer; D008722:Methods; D011282:Pregnenediones / Q000138:chemical synthesis*
C016226:21-amino-5-pregnene-3,20-dione bisethylene ketal; D011282:Pregnenediones