467-14-1Relevant articles and documents
Synthesis of neopine and its 5β- and 7-substituted derivatives (chemistry of opium alkaloids, part XL)
Meuzelaar, G. J.,Woudenberg, R. H.,Sinnema, A.,Maat, L.
, p. 573 - 577 (1993)
Heating 14β-bromocodeine (3) with methanol and triethylamine yielded 6α,7α-epoxy-6-deoxyneopine (5).The epoxide 5 was reduced to neopine (7) with lithium aluminium hydride, whereas reaction of 5 with sodium methoxide gave 7β-methoxyneopine (9).Similar reactions were performed with 14β-bromo-5β-methylcodeine (4), yielding the corresponding 5β-methyl derivatives 6, 8 and 10.Acetylation of 3 and 4 gave 6α-O-acetyl-14β-bromocodeine (11) and its 5β-methyl analogue 12, respectively, from which the ortho esters 13 and 14 were obtained after treatment with methanol.Acid hydrolysis of 13 or, better, solvolysis of 11 in water yielded a mixture of 6α-O-acetyl-7α-hydroxyneopine (15) and 7α-acetoxyneopine (17).Under the same conditions 12 and 14 gave the 5β-methyl analogues 16 and 18.
Selective reductions of neopinone to neopine and isoneopine
Wunderly,Brochmann Hanssen
, p. 4277 - 4278 (1977)
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METHOD FOR THE CATALYTIC PRODUCTION OF HYDROCODONE AND HYDROMORPHONE
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Page/Page column 7, (2008/06/13)
A method for the catalytic conversion of codeine, morphine or analogs thereof into hydrocodone, hydromorphone or analogs thereof utilizing a transition metal complex of a tertiary phosphine halide as catalyst.
Isoneopine from Thebaine
Seyed-Mozaffari, Ahmad,Archer, Sydney
, p. 2444 - 2445 (2007/10/02)
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