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药物详细合成路线

Name Minaxolone
Chemical Name (2beta,3alpha,5alpha,11alpha)-11-Dimethylamino-2-ethoxy-3-hydroxypregnan-20-one
CAS 62571-87-3
Related CAS
Formula C25H43NO3
Structure
Formula Weight 405.62636
Stage 未确定
Company GlaxoSmithKline (Originator)
Activity/Mechanism ANALGESIC AND ANESTHETIC DRUGS, Anesthetic Drugs
Syn. Route 1
Route 1
the ketalization of 2beta-ethoxy-3alpha-hydroxy-5alpha-pregnane-11,20-dione (i) with ethylene glycol (a) by means of p-toluenesulfonic acid in refluxing benzene gives the corresponding 20,20-ethylenedioxy derivative (ii), which is treated with hydroxylamine hydrochloride and naoh refluxing ethanol to yield 20,20-ethylenedioxy-2beta-ethoxy-3alpha-hydroxy-5alpha-pregnan-11-one 11-oxime (iii). the reduction of (iii) with na in refluxing propanol (b) affords 11alpha-amino-20,20-ethylenedioxy-2beta-ethoxy-3alpha-hydroxy-5alpha-pregnan (iv), which is finally methylated with methyl iodide and k2co3 or with formaldehyde and formic acid, and hydrolyzed with hcl or h2so4.
List of intermediates No.
(1r,4as,10ar)-7-isopropyl-1,4a-dimethyl-6-sulfo-1,2,3,4,4a,9,10,10a-octahydro-1-phenanthrenecarboxylic acid (ai)
4,6-dimethyl-2-pyridinamine; 4,6-dimethyl-2-pyridinylamine (b)
(3r,4s,6s,9as)-4-methyl-6-[(1e,3e)-1,3-octadienyl]octahydro-2h-quinolizin-3-ol (i)
(4ar,6as,10s,11as)-3,3-dimethyl-10-[(phenylsulfonyl)methyl]decahydro[1,3]dioxino[4,5-c]quinolizine; [(4ar,6as,10s,11as)-3,3-dimethyldecahydro[1,3]dioxino[4,5-c]quinolizin-10-yl]methyl phenyl sulfone (ii)
[(3r,4s,6s,9as)-3-(methoxymethoxy)-6-[(phenylsulfonyl)methyl]octahydro-2h-quinolizin-4-yl]methanol (iii)
(3r,4s,6s,9as)-6-[(1e,3e)-1,3-decadienyl]-4-methyloctahydro-2h-quinolizin-3-yl methoxymethyl ether; (3r,4s,6s,9as)-6-[(1e,3e)-1,3-decadienyl]-3-(methoxymethoxy)-4-methyloctahydro-2h-quinolizine (iv)
Reference 1:
    philips, g.h.; ewan, g.; de 2715078 .
Reference 2:
    hillier, k.; castaner, j.; blancafort, p.; serradell, m.n.; minaxolone. drugs fut 1980, 5, 12, 614.

 
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