Dihydronarwedine

Base Information

• Chemical Name: Dihydronarwedine
• CAS No.: 21041-10-1
• Molecular Formula: C₁₇H₂₁NO₃
• Molecular Weight: 287.359
• Mol file: 21041-10-1.mol

Synonyms:Dihydronarwedine;Dihydro GalantaMinone HCl

Chemical Property of Dihydronarwedine

Chemical Property:

• Melting Point: 130 - 132 °C (ethanol)
• PSA: 38.77000
• LogP: 2.22040

Purity/Quality:

99% ^*data from raw suppliers

Dihydronarwedine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: Dihydronarwedine is a metabolite of Galanthamine (G188500), a selective acetylcholinesterase inhibitor and therapeutic agent for the treatment and prevention of Alzheimer’s disease and disorders resulting from reduced neuronal metabolism.

Technology Process of Dihydronarwedine

There total 1 articles about Dihydronarwedine 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:

C17H18BrNO3 → (4aS,8aS)-rel-3-methoxy-11-methyl-4a,5,9,10,11,12-hexahydro-6H-benzo[2,3]benzofuro[4,3-cd]azepin-6-one (510-77-0,1668-86-6,7318-55-0,26601-10-5) + (4aS,8aR)-3-methoxy-11-methyl-4a,5,7,8,9,10,11,12-octahydro-6H-benzo[2,3]benzofuro-[4,3-cd]azepin-6-one (2658-88-0,21041-10-1,21041-17-8)

Guidance literature:

With ethanol; zinc; at 20 - 75 ℃; for 9h; Inert atmosphere;

DOI:10.1021/ol100617u

Reference yield: 45.0%

(4aS,8aR)-3-methoxy-11-methyl-4a,5,7,8,9,10,11,12-octahydro-6H-benzo[2,3]benzofuro-[4,3-cd]azepin-6-one (2658-88-0,21041-10-1,21041-17-8) → (4aS,8aS)-rel-3-methoxy-11-methyl-4a,5,9,10,11,12-hexahydro-6H-benzo[2,3]benzofuro[4,3-cd]azepin-6-one (510-77-0,1668-86-6,7318-55-0,26601-10-5)

Guidance literature:

(4aS,8aR)-3-methoxy-11-methyl-4a,5,7,8,9,10,11,12-octahydro-6H-benzo[2,3]benzofuro-[4,3-cd]azepin-6-one; With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; for 0.5h; Inert atmosphere;

With diphenyldisulfane; In tetrahydrofuran; at -78 - 0 ℃; for 2h; Further stages;

DOI:10.1039/c8ob03123a

Reference yield:

(4aS,8aR)-3-methoxy-11-methyl-4a,5,7,8,9,10,11,12-octahydro-6H-benzo[2,3]benzofuro-[4,3-cd]azepin-6-one (2658-88-0,21041-10-1,21041-17-8) → galanthamine (357-70-0,1668-85-5,23173-12-8,23173-13-9,60384-53-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: lithium diisopropyl amide / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

1.2: 2 h / -78 - 0 °C

2.1: lithium tri-sec-butyl(hydrido)borate / tetrahydrofuran / -78 - 20 °C / Inert atmosphere

With lithium tri-sec-butyl(hydrido)borate; lithium diisopropyl amide; In tetrahydrofuran;

DOI:10.1039/c8ob03123a

Downstream raw materials:

(4aS,8aS)-rel-3-methoxy-11-methyl-4a,5,9,10,11,12-hexahydro-6H-benzo[2,3]benzofuro[4,3-cd]azepin-6-one

galanthamine

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