【药物名称】Dezocine, Wy-16225, Dalgan
化学结构式(Chemical Structure):
参考文献No.65752
标题:Dezocine
作者:Hopkins, S.J.; Casta馿r, J.
来源:Drugs Fut 1976,1(5),229
合成路线图解说明:

Compound is prepared through the following sequence: The condensation of 1-methyl-7-methoxy-2-tetralone (I) with 1,5-dibromopentane (A) by means of NaH or potassium tertbutylate affords 1-(5-bromopentyl)-1-methyl-7-methoxy-2-tetralone (II); this product is cyclized with NaH to give 5-methyl-3-methoxy-5,6,7,8,9,10,11,12-octahydro-5,11-methanobenzocyclodecen-13-one (III). The ketone (III), by reaction with hydroxylamine hydrochloride in pyridine, is converted into its oxime (IV), which is reduced with H2 over Raney-Ni to a mixture of isomeric amines that were separated by crystallization of the HCl salts giving 5alpha-methyl-3-methoxy-5,6,7,8,9,11alpha,12-octahydro-5,11-methanobenzocyclodecen-13beta-amine (V), which is finally submitted to cleavage with concentrated HBr.

参考文献No.607777
标题:Bridged aminotetralins as novel potent analgesic substances
作者:Freed, M.E.; Potoski, J.R.; Freed, E.H.; Conklin, G.L.; Malis, J.L.
来源:J Med Chem 1973,16(6),595
合成路线图解说明:

Compound is prepared through the following sequence: The condensation of 1-methyl-7-methoxy-2-tetralone (I) with 1,5-dibromopentane (A) by means of NaH or potassium tertbutylate affords 1-(5-bromopentyl)-1-methyl-7-methoxy-2-tetralone (II); this product is cyclized with NaH to give 5-methyl-3-methoxy-5,6,7,8,9,10,11,12-octahydro-5,11-methanobenzocyclodecen-13-one (III). The ketone (III), by reaction with hydroxylamine hydrochloride in pyridine, is converted into its oxime (IV), which is reduced with H2 over Raney-Ni to a mixture of isomeric amines that were separated by crystallization of the HCl salts giving 5alpha-methyl-3-methoxy-5,6,7,8,9,11alpha,12-octahydro-5,11-methanobenzocyclodecen-13beta-amine (V), which is finally submitted to cleavage with concentrated HBr.

参考文献No.701127
标题:Benzobicycloalkanes compounds
作者:Freed, M.E.; Potoski, J.R.
来源:DE 2159324; FR 2116509; GB 1363658; GB 1363659
合成路线图解说明:

Compound is prepared through the following sequence: The condensation of 1-methyl-7-methoxy-2-tetralone (I) with 1,5-dibromopentane (A) by means of NaH or potassium tertbutylate affords 1-(5-bromopentyl)-1-methyl-7-methoxy-2-tetralone (II); this product is cyclized with NaH to give 5-methyl-3-methoxy-5,6,7,8,9,10,11,12-octahydro-5,11-methanobenzocyclodecen-13-one (III). The ketone (III), by reaction with hydroxylamine hydrochloride in pyridine, is converted into its oxime (IV), which is reduced with H2 over Raney-Ni to a mixture of isomeric amines that were separated by crystallization of the HCl salts giving 5alpha-methyl-3-methoxy-5,6,7,8,9,11alpha,12-octahydro-5,11-methanobenzocyclodecen-13beta-amine (V), which is finally submitted to cleavage with concentrated HBr.

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