(4aR,6S,8aR)-4a,5,9,10,11,12-hexahydro-3-methoxy-11-methyl-6H-benzofuro[3a,3,2-ef][2] benzazepine-6-ol hydrobromide

Base Information

• Chemical Name: (4aR,6S,8aR)-4a,5,9,10,11,12-hexahydro-3-methoxy-11-methyl-6H-benzofuro[3a,3,2-ef][2] benzazepine-6-ol hydrobromide
• CAS No.: 1556014-63-1
• Molecular Formula: BrH*C₁₇H₂₁NO₃
• Molecular Weight: 368.271
• Mol file: 1556014-63-1.mol

Synonyms:

Chemical Property of (4aR,6S,8aR)-4a,5,9,10,11,12-hexahydro-3-methoxy-11-methyl-6H-benzofuro[3a,3,2-ef][2] benzazepine-6-ol hydrobromide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4aR,6S,8aR)-4a,5,9,10,11,12-hexahydro-3-methoxy-11-methyl-6H-benzofuro[3a,3,2-ef][2] benzazepine-6-ol hydrobromide

There total 6 articles about (4aR,6S,8aR)-4a,5,9,10,11,12-hexahydro-3-methoxy-11-methyl-6H-benzofuro[3a,3,2-ef][2] benzazepine-6-ol hydrobromide 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: 85.4%

(4aR,8aR)-4a,5,9,10,11,12-hexahydro-3-methoxy-11-methyl-6H-benzofuro[3a,3,2-ef][2]benzazepin-6-one (7318-55-0,26601-10-5) → (4aR,6S,8aR)-4a,5,9,10,11,12-hexahydro-3-methoxy-11-methyl-6H-benzofuro[3a,3,2-ef][2] benzazepine-6-ol hydrobromide (1556014-63-1,193146-85-9)

Guidance literature:

(4aR,8aR)-4a,5,9,10,11,12-hexahydro-3-methoxy-11-methyl-6H-benzofuro[3a,3,2-ef][2]benzazepin-6-one; With L-Selectride; In tetrahydrofuran; at -50 - -45 ℃; for 4h;

With hydrogen bromide; In ethanol; water; at 15 - 20 ℃; for 2h; diastereoselective reaction;

DOI:10.1016/j.tetasy.2013.11.016

Reference yield: 69.0%

(4aR,8aR)-4a,5,9,10,11,12-hexahydro-3-methoxy-11-methyl-6H-benzofuro[3a,3,2-ef][2]benzazepin-6-one (7318-55-0,26601-10-5) → (4aR,6R,8aR)-4a,5,9,10,11,12-hexahydro-3-methoxy-11-methyl-6H-benzofuro[3a,3,2-ef][2] benzezapine-6-ol (261961-58-4) + (4aR,6S,8aR)-4a,5,9,10,11,12-hexahydro-3-methoxy-11-methyl-6H-benzofuro[3a,3,2-ef][2] benzazepine-6-ol hydrobromide (1556014-63-1,193146-85-9)

Guidance literature:

(4aR,8aR)-4a,5,9,10,11,12-hexahydro-3-methoxy-11-methyl-6H-benzofuro[3a,3,2-ef][2]benzazepin-6-one; With cerium(III) chloride heptahydrate; In methanol; dichloromethane; at -55 - 50 ℃; for 0.5h;

With sodium tetrahydroborate; In methanol; dichloromethane; at -55 - -50 ℃; for 2.5h;

DOI:10.1016/j.tetasy.2013.11.016

Reference yield:

(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) → (4aR,6S,8aR)-4a,5,9,10,11,12-hexahydro-3-methoxy-11-methyl-6H-benzofuro[3a,3,2-ef][2] benzazepine-6-ol hydrobromide (1556014-63-1,193146-85-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: triethylamine / water; ethanol / 3 h / 25 - 73 °C / Resolution of racemate

2.1: L-Selectride / tetrahydrofuran / 4 h / -50 - -45 °C

2.2: 2 h / 15 - 20 °C

With L-Selectride; triethylamine; In tetrahydrofuran; ethanol; water;

DOI:10.1016/j.tetasy.2013.11.016

upstream raw materials:

(4aR,8aR)-4a,5,9,10,11,12-hexahydro-3-methoxy-11-methyl-6H-benzofuro[3a,3,2-ef][2]benzazepin-6-one

(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

(-)-narwedine