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药物详细合成路线

Name Aminoglutethimide;AG-1;Orimeten;Cytadren
Chemical Name 3-(4-Aminophenyl)-3-ethyl-2,6-piperidinedione
CAS 125-84-8
Related CAS
Formula C13H16N2O2
Structure
Formula Weight 232.28467
Stage 上市-1981
Company Novartis (Originator)
Activity/Mechanism Adrenocortical Dysfunction Therapy, Breast Cancer Therapy, Cushings Syndrome, Agents for, ENDOCRINE DRUGS, Oncolytic Drugs, Prostate Cancer Therapy, Antiglucocorticoids, Aromatase Inhibitors
Syn. Route 1
Route 1
an improved procedure for the large-scale preparation of (r)-aminoglutethimide has been reported. nucleophilic substitution of 1-chloro-4-nitrobenzene (i) with methyl cyanoacetate afforded the (nitrophenyl)cyanoacetate (ii), which was alkylated with diethyl sulfate in the presence of et3n, yielding (iii). hydrolysis and decarboxylation of the cyano ester (iii) by means of k2co3 in aqueous meoh provided the arylbutyronitrile (iv). subsequent michael addition with methyl acrylate gave adduct (v). this was hydrolyzed to the cyano acid (vi), which was further resolved with (-)-cinchonidine, yielding the desired (r)-enantiomer (vii). acid-catalyzed cyclization of (vii) in boiling toluene generated the glutarimide derivative (viii). the nitro group of (viii) was finally reduced to the title amino derivative by hydrogenation over pd/c.
List of intermediates No.
(4s,7r,8s,9s,16s)-8-hydroxy-5,5,7,9,13-pentamethyl-16-[(e)-1-methyl-2-(2-methyl-1,3-thiazol-4-yl)ethenyl]-4-[(triethylsilyl)oxy]oxa-13-cyclohexadecene-2,6-dione (i)
1-methyl-2-oxo-1,2-dihydro-4-pyridinecarbaldehyde
2-(2-phenyl-1h-indol-3-yl)-1-ethanamine; 2-(2-phenyl-1h-indol-3-yl)ethylamine
(1as,8r,9as)-3-(acetoxy)-7-(benzyloxy)-5-[[(benzyloxy)methoxy]methyl]-8-(hydroxymethyl)-1-[(4-methylphenyl)sulfonyl]-1,1a,2,3,8,9a-hexahydro-9h-azireno[2,3-c][1]benzazocin-9-one (ii)
(1as,8r,9as)-7-(benzyloxy)-5-[[(benzyloxy)methoxy]methyl]-3-hydroxy-8-(hydroxymethyl)-1-[(4-methylphenyl)sulfonyl]-1,1a,2,3,8,9a-hexahydro-9h-azireno[2,3-c][1]benzazocin-9-one (iii)
(8r,9s,10s,12s)-6-(benzyloxy)-4-[[(benzyloxy)methoxy]methyl]-8-(hydroxymethyl)-11-[(4-methylphenyl)sulfonyl]-14-oxa-1,11-diazatetracyclo[7.4.1.0(2,7).0(10,12)]tetradeca-2,4,6-trien-9-ol (iv)
(1s,6r,15s,17s)-8-(benzyloxy)-10-[[(benzyloxy)methoxy]methyl]-16-[(4-methylphenyl)sulfonyl]-2,4,18-trioxa-13,16-diazapentacyclo[11.4.1.0(1,6).0(7,12).0(15,17)]octadeca-7,9,11-trien-3-one (v)
[(8r,9s,10s,12s)-6-(benzyloxy)-4-[[(benzyloxy)methoxy]methyl]-9-hydroxy-11-[(4-methylphenyl)sulfonyl]-14-oxa-1,11-diazatetracyclo[7.4.1.0(2,7).0(10,12)]tetradeca-2,4,6-trien-8-yl]methyl carbamate (vi)
(8r,10s,12s)-8-[[(aminocarbonyl)oxy]methyl]-6-(benzyloxy)-4-[[(benzyloxy)methoxy]methyl]-11-[(4-methylphenyl)sulfonyl]-14-oxa-1,11-diazatetracyclo[7.4.1.0(2,7).0(10,12)]tetradeca-2,4,6-trien-9-yl acetate (vii)
(8r,10s,12s)-8-[[(aminocarbonyl)oxy]methyl]-6-(benzyloxy)-4-[[(benzyloxy)methoxy]methyl]-14-oxa-1,11-diazatetracyclo[7.4.1.0(2,7).0(10,12)]tetradeca-2,4,6-trien-9-yl acetate (viii)
Reference 1:
    bunegar, m.j.; et al.; production of (r)-aminogluthimide: a new route from 1-chloro-4-nitrobenzene. org process res dev 1999, 3, 6, 442.

 
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