Morphinan-3,14-diol,6-amino-4,5-epoxy-17- methyl-,(5R,6R)-

Base Information

• Chemical Name: Morphinan-3,14-diol,6-amino-4,5-epoxy-17- methyl-,(5R,6R)-
• CAS No.: 98634-03-8
• Molecular Formula: C₁₇H₂₂N₂O₃
• Molecular Weight: 302.373
• Mol file: 98634-03-8.mol

Synonyms:

Chemical Property of Morphinan-3,14-diol,6-amino-4,5-epoxy-17- methyl-,(5R,6R)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Morphinan-3,14-diol,6-amino-4,5-epoxy-17- methyl-,(5R,6R)-

There total 5 articles about Morphinan-3,14-diol,6-amino-4,5-epoxy-17- methyl-,(5R,6R)- which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

C17H20N2O3 → 6β-oxymorphamine (72782-04-8,84800-62-4) + (5α,6α)-6-amino-4,5-epoxy-3,14-dihydroxy-17-methylmorphinan (98634-03-8,84800-62-4)

Guidance literature:

With sodium cyanoborohydride; In methanol; at 20 ℃; Inert atmosphere;

DOI:10.1016/j.bmcl.2011.05.008

Reference yield:

C24H28N2O3 (1257541-93-7) → (5α,6α)-6-amino-4,5-epoxy-3,14-dihydroxy-17-methylmorphinan (98634-03-8,84800-62-4)

Guidance literature:

With 5% Pd/C; hydrogen; In methanol; for 72h; under 2068.65 Torr;

DOI:10.1021/ml300083p

Reference yield:

oxymorphone hydrochloride (357-07-3) → (5α,6α)-6-amino-4,5-epoxy-3,14-dihydroxy-17-methylmorphinan (98634-03-8,84800-62-4)

Guidance literature:

Multi-step reaction with 4 steps

1: sodium carbonate / water / 1 h / pH 9

2: toluene-4-sulfonic acid / benzene / 10 h / Reflux; Dean-Stark

3: sodium tetrahydroborate / ethanol / 3 h / Reflux

4: 5% Pd/C; hydrogen / methanol / 72 h / 2068.65 Torr

With sodium tetrahydroborate; 5% Pd/C; hydrogen; sodium carbonate; toluene-4-sulfonic acid; In methanol; ethanol; water; benzene;

DOI:10.1021/ml300083p

upstream raw materials:

oxymorphone hydrochloride

C₂₄H₂₆N₂O₃

C₂₄H₂₈N₂O₃

oxymorphone

Downstream raw materials:

5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-N-(1-(19-(((4αS,7S,7αR,12βS)-4α,9-dihydroxy-3-methyl-2,3,4,4α,5,6,7,7α-octahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-yl)amino)-5,15,19-trioxo-3,17-dioxa-6,14-diazanonadecan-1-oyl)piperidin-4-yl)-4-methyl-1H-pyrazole-3-carboxamide

5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-N-(1-(18-(((4αS,7-S,7αR,12βS)-4α,9-dihydroxy-3-methyl-2,3,4,4α,5,6,7,7α-octahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-yl)amino)-5,14,18-trioxo-3,16-dioxa-6,13-diazaoctadecan-1-oyl)piperidin-4-yl)-4-methyl-1H-pyrazole-3-carboxamide

5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-N-(1-(14-(((4αS,7S,7αR,12βS)-4α,9-dihydroxy-3-methyl-2,3,4,4α,5,6,7,7α-octahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-yl)amino)-5,10,14-trioxo-3,12-dioxa-6,9-diazatetradecan-1-oyl)piperidin-4-yl)-4-methyl-1H-pyrazole-3-carboxamide

5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-N-(1-(2-(2-(((4αS,7S,7αR,12βS)-4α,9-dihydroxy-3-methyl-2,3,4,4α,5,6,7,7α-octahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-yl)amino)-2-oxoethoxy)acetyl)piperidin-4-yl)-4-methyl-1H-pyrazole-3-carboxamide

Refernces

• 1、 Majumdar, Susruta,Burgman, Maxim,Haselton, Nathan,Grinnell, Steven,Ocampo, Julia,Pasternak, Anna Rose,Pasternak, Gavril W.. "Generation of novel radiolabeled opiates through site-selective iodination". supporting information; experimental part. p. 4001 - 4004. Retrieved 2011/08/06.