5088-64-2Relevant academic research and scientific papers
Studies in the syntheses of some potential neuromuscular blocking azasteroids
Yadav, Mange Ram
, p. 746 - 753 (2007/10/02)
The potential neuromuscular blocking azasteroids 17, 18 and 27 have been synthesised by different routes. α-Oximino hydrazone 1 on reduction gives 2, which on Beckmann rearrangement gives lactam 3 as the major product.Sodium/n-pentanol reduction of the lactam function in 3 and N-methylation of the resulting amine 5 affords 7.Oppenauer oxidation of 7 followed by pyrrolidine treatment gives the enamine 8 which is reduced by sodium borohydride to 9.Compound 9 is also obtained through another similar sequence of reactions using lactam 3.Compound 3 is subjected to Oppenauer oxidation followed by pyrrolidine treatment and sodium borohydride reduction to yield 12, which is reduced by sodium/n-pentanol to give amine 13.The amine 13 is N-methylated by formaldehyde/sodium borohydride to 9.The intermediate 12 is also obtained starting from 3β-pyrrolidino-5-androsten-17-one.On nitrosation in alkaline medium it gives 14, which on hydrazine hydrate treatment affords 15.Compound 15 on reduction and Beckmann rearrangement gives 12.The tertiary amine 9 when quaternised with methyl iodide affords 17 and with allyl bromide 18.The other bisquaternary ammonium compound 27 is prepared starting from oxime 2.Compound 2 on sodium/n-pentanol reduction and N-methylation yields 23 on chromatographic purification.Oppenauer oxidation followed by pyrrolidine treatment and sodium borohydride reduction of 23 gives 26 which is quaternised to 27.
