65494-41-9

Upstream product

• 6080-33-7 Sinomenine Hydrochloride 

Downstream Products

• 1160816-08-9 4-benzyl-dihydrosinomenine 
• 73079-28-4 (+)-4,5-Epoxy-7-oxo-3-methoxy-17-methylmorphinan 
• 73079-27-3 (+)-4-Hydroxy-7-oxo-3-methoxy-17-methyl-5,6-dehydromorphinan 
• 125-29-1 dihydrocodeinone 

Relevant academic research and scientific papers

Process and compounds for the production of (+)opiates

The invention generally provides processes and intermediate compounds useful for the production of (+)-opiates. Non-limiting examples of (+) opiates that may be derived from one or more compounds of the invention include (+)-noroxymorphone, (+)-naltrexone, (+)-naloxone, (+)-N-cyclopropylmethylnorhydrocodone, (+)-N-cycloproylmethylnorhydromorphone, (+)-N-allylnorhydrocodone, (+)-N-allylnorhydromorphone, (+)-noroxycodone, (+)-naltrexol, (+)-naloxol, and (+)-3-O-methyl-naltrexone.

PROCESS FOR THE PRODUCTION OF (+)-MORPHINE

The invention relates to a process for the production of (+)-morphine from (-)-sinomenine comprising contacting (-)-sinomenine with H2/Pd/C under conditions effective for converting sinomenine to 7(S)-(+)-dihydrosinomenine or 7(R)-(+)-dihydrosinomenine or a mixture thereof; contacting the resulting 7(S)-(+)-dihydrosinomenine or 7(R)-(+)-dihydrosinomenine or a mixture thereof with polyphosphoric acid or Eatons reagent under conditions effective for converting 7(S)-(+)-dihydrosinomenine or 7(R)-(+)-dihydrosinomenine or a mixture thereof to (+)-dihydrocodeinone; contacting the resulting (+)-dihydrocodeinone either with (MeO)3CH followed by TsOH followed by NBA/MeOH under conditions effective for converting (+)-dihydrocodeinone to (+)-1,7-dibromodihydrocodeinone dimethylketal; contacting the resulting (+)-1,7-dibromodihydrocodeinone dimethylketal with t-butoxide followed by acid under conditions effective for converting (+)-1,7-dibromodihydrocodeinone dimethylketal to (+)-1-bromocodeinone; contacting the resulting (+)-1-bromocodeinone with LiAlH4 followed by BBr3 under conditions effective for converting (+)-1-bromocodeinone to (+)-morphine; or with o-iodoxybenzoic acid (IBX) and 4-methoxypyridine-N-oxide under conditions effective for converting (+)-dihydrocodeinone to (+)-codeinone; contacting the resulting (+)-codeinone with sodium borohydride followed by BBr3 under conditions effective for converting (+)-codeinone to (+)-morphine; and in either case recovering the resulting (+)-morphine as product. The invention also relates to novel compounds produced during the process.