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 3 beta-methoxypregnenolone (MAP4343). The use of Proton Sponge (TM), 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.

A streamlined synthesis of the neurosteroid 3β-methoxypregnenolone assisted by a statistical experimental design and automation

Valentina Mancino
Investigation
;
Federico Croci
Investigation
;
Anna Maria Lozza
Writing – Review & Editing
;
Bruno Cerra
Supervision
;
Antimo Gioiello
Project Administration
2020

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 3 beta-methoxypregnenolone (MAP4343). The use of Proton Sponge (TM), 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.
2020
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11391/1461891
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