(4aS,6R,8aS)-11-butyl-4a,5,9,10,11,12-hexahydro-3-methoxy-6H-[1]benzofuro[3a,3,2-ef][2]benzazepin-6-ol

Base Information

• Chemical Name: (4aS,6R,8aS)-11-butyl-4a,5,9,10,11,12-hexahydro-3-methoxy-6H-[1]benzofuro[3a,3,2-ef][2]benzazepin-6-ol
• CAS No.: 550346-82-2
• Molecular Formula: C₂₀H₂₇NO₃
• Molecular Weight: 329.439

Synonyms:(4aS,6R,8aS)-11-butyl-4a,5,9,10,11,12-hexahydro-3-methoxy-6H-[1]benzofuro[3a,3,2-ef][2]benzazepin-6-ol

Chemical Property of (4aS,6R,8aS)-11-butyl-4a,5,9,10,11,12-hexahydro-3-methoxy-6H-[1]benzofuro[3a,3,2-ef][2]benzazepin-6-ol

Chemical Property:

Purity/Quality:

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Technology Process of (4aS,6R,8aS)-11-butyl-4a,5,9,10,11,12-hexahydro-3-methoxy-6H-[1]benzofuro[3a,3,2-ef][2]benzazepin-6-ol

There total 2 articles about (4aS,6R,8aS)-11-butyl-4a,5,9,10,11,12-hexahydro-3-methoxy-6H-[1]benzofuro[3a,3,2-ef][2]benzazepin-6-ol 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:

(4aS,6R,8aS,11S)-4a,5,9,10,11,12-hexahydro-6-hydroxy-3-methoxy-11-methyl-11-butyl-6H-[1]benzofuro[3a,3,2-ef][2]benzazepin-11-ium iodide → Galantamine (357-70-0) + (3R,4aS,9bS)-9b-[2-(Butyl-methyl-amino)-ethyl]-6-methoxy-9-methyl-3,4,4a,9b-tetrahydro-dibenzofuran-3-ol + (4aS,6R,8aS)-11-butyl-4a,5,9,10,11,12-hexahydro-3-methoxy-6H-[1]benzofuro[3a,3,2-ef][2]benzazepin-6-ol (550346-82-2)

Guidance literature:

With lithium triethylborohydride; In tetrahydrofuran; at 65 ℃; for 5h;

DOI:10.1016/S0957-4166(03)00116-2

Reference yield:

(4aS,6R,8aS,11R)-4a,5,9,10,11,12-hexahydro-6-hydroxy-3-methoxy-11-methyl-11-butyl-6H-[1]benzofuro[3a,3,2-ef][2]benzazepin-11-ium iodide → Galantamine (357-70-0) + (3R,4aS,9bS)-9b-[2-(Butyl-methyl-amino)-ethyl]-6-methoxy-9-methyl-3,4,4a,9b-tetrahydro-dibenzofuran-3-ol + (4aS,6R,8aS)-11-butyl-4a,5,9,10,11,12-hexahydro-3-methoxy-6H-[1]benzofuro[3a,3,2-ef][2]benzazepin-6-ol (550346-82-2)

Guidance literature:

With lithium triethylborohydride; In tetrahydrofuran; at 65 ℃; for 5h;

DOI:10.1016/S0957-4166(03)00116-2

Reference yield:

(4aS,6R,8aS)-11-butyl-4a,5,9,10,11,12-hexahydro-3-methoxy-6H-[1]benzofuro[3a,3,2-ef][2]benzazepin-6-ol (550346-82-2) → Galantamine (357-70-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 94 percent / dimethylformamide / 0.33 h / 25 °C

2: 85 percent Chromat_. / Super Hydride(R) / tetrahydrofuran / 5 h / 65 °C

With lithium triethylborohydride; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1016/S0957-4166(03)00116-2

Downstream raw materials:

Galantamine

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