76787-06-9

Upstream product

• 80907-82-0 1-<3,5-bis(benzyloxy)benzyl>-6-methoxy-3,4-dihydroisoquinoline hydrochloride 
• 76787-08-1 1-(3',5'-dibenzyloxybenzyl)-6-methoxy-1,2,3,4-tetrahydroisoquinoline 
• 2732-96-9 3,5-dibenzyloxyphenylacetic acid 
• 80907-81-9 N-(3-methoxyphenethyl)-2-<3,5-bis(benzyloxy)phenyl>acetamide 
• 79087-59-5 1-<3',5-bis(benzyloxy)benzyl>-6-methoxy-3,4-dihydroisoquinoline 

Downstream Products

• 76787-05-8 1-(3',5'-dihydroxybenzyl)-2-formyl-6-methoxy-1,2,3,4,5,8-hexahydroisoquinoline 

Relevant academic research and scientific papers

Total Synthesis of (+/-)-3-Deoxy-7,8-dihydromorphinone

The total synthesis of (+/-)-3-deoxy-7,8-dihydromorphinone (1), starting from readily available acetic acid (4) is described.The amide 6, obtained from acid 4 and m-methoxyphenethylamine was converted by Bischler-Napieralski cyclization to the dihydroisoquinoline hydrochloride 7.Birch reduction of 7 gave the dihydroxydihydroanisole 8, which was acid cyclized in situ and then converted to (+/-)-2,4-bis-17-(methoxycarbonyl)morphinan-6-one (10).The conversion of 7 to 10 was carried out without isolation of intermediates.Hydrolysis with THF/Et2NH gave the 4-hydroxy compound 14.Reaction of 14 with cupric bromide followed by treatment with NaOH/CHCl3 and hydrolysis gave 4,5-epoxy-2-hydroxymorphinan-6-one (16).The 2-oxygen function was removed by Li/NH3 reduction of the phosphate ester 18 obtained by acylation of the ketal 17 with diethyl chlorophosphate.LAH reduction of the ketal 19 followed by acid hydrolysis gave the title compound (+/-)-3-deoxy-7,8-dihydromorphinone (1) in an overall yield (from 4) of 27percent.