A streamlined synthesis of the neurosteroid 3β-methoxypregnenolone assisted by a statistical experimental design and automation. Issue 2 (5th December 2019)

• Record Type: Journal Article
• Authors: Mancino, Valentina; Croci, Federico; Lozza, Anna Maria; Cerra, Bruno; Gioiello, Antimo
• Is Part Of: Reaction chemistry & engineering. Volume 5:Issue 2(2020)
• Page Start: 300
• Page End: 307
• Publication Date: 2019-12-05
• Subjects: Reaction mechanisms (Chemistry) -- Periodicals; Chemical engineering -- Periodicals; Chemical engineering; Reaction mechanisms (Chemistry); Periodicals; 547.705
• DOI: 10.1039/c9re00353c
• Languages: English
• ISSNs: 2058-9883

Abstract

Abstract : The potential of integrating flow synthesizers, statistical design of experiments and automation has been exemplified to realize the streamlined etherification of pregnenolone to the neurosteroid 3β-methoxypregnenolone (MAP4343). Abstract : The potential of integrating flow synthesizers, statistical design of experiments and automation has been exemplified to realize the streamlined etherification of pregnenolone to the neurosteroid 3β-methoxypregnenolone (MAP4343). The use of Proton Sponge™, online reaction monitoring, work-up, product purification, and reagent recovery are additional key features of the present study. The optimized single-step process was validated by conducting a multistep sequence that has enabled the continuous flow synthesis of MAP4343 on a laboratory scale with an overall yield of 64% via six steps from the readily available plant-derived diosgenin.