(2S,4R)-2,4-bis(4-bromophenyl)-2-methyl-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepine

Base Information

• Chemical Name: (2S,4R)-2,4-bis(4-bromophenyl)-2-methyl-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepine
• CAS No.: 1176195-99-5
• Molecular Formula: C₂₂H₂₀Br₂N₂
• Molecular Weight: 472.222

Synonyms:(2S,4R)-2,4-bis(4-bromophenyl)-2-methyl-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepine

Chemical Property of (2S,4R)-2,4-bis(4-bromophenyl)-2-methyl-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepine

Chemical Property:

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Technology Process of (2S,4R)-2,4-bis(4-bromophenyl)-2-methyl-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepine

There total 3 articles about (2S,4R)-2,4-bis(4-bromophenyl)-2-methyl-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepine 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:

2,4-bis(4-bromophenyl)-2-methyl-2,3-dihydro-1H-benzo[b][1,4]diazepine (89586-99-2) → C22H20Br2N2 + (2S,4S)-2,4-bis(4-bromophenyl)-2-methyl-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepine (1176196-27-2) + (2S,4R)-2,4-bis(4-bromophenyl)-2-methyl-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepine (1176195-99-5)

Guidance literature:

With C₁₂H₁₀O₄P^(1-)*C₂₅H₃₁N₂O₂RuS⁽¹⁺⁾; hydrogen; In dichloromethane; at 40 ℃; for 10h; under 38002.6 Torr; stereoselective reaction; Autoclave; Glovebox;

DOI:10.1002/ejoc.201700236

Reference yield:

2,4-bis(4-bromophenyl)-2-methyl-2,3-dihydro-1H-benzo[b][1,4]diazepine (89586-99-2) → C22H20Br2N2 + C22H20Br2N2 + (2S,4S)-2,4-bis(4-bromophenyl)-2-methyl-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepine (1176196-27-2) + (2S,4R)-2,4-bis(4-bromophenyl)-2-methyl-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepine (1176195-99-5)

Guidance literature:

With 4-hydroxy-2,6-diphenyl-8,9,10,11,12,13,14,15-octahydrodinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepine 4-oxide; diallyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; sodium sulfate; In chloroform; at -10 ℃; for 132h; optical yield given as %ee; enantioselective reaction;

DOI:10.1016/j.bmcl.2009.05.039

Reference yield:

para-bromoacetophenone (99-90-1) + 1,2-diamino-benzene (95-54-5) → C22H20Br2N2 + (2S,4S)-2,4-bis(4-bromophenyl)-2-methyl-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepine (1176196-27-2) + (2S,4R)-2,4-bis(4-bromophenyl)-2-methyl-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepine (1176195-99-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 1,3,5-trichloro-2,4,6-triazine / toluene / 10 h / 45 °C / Inert atmosphere

2: hydrogen; C₁₂H₁₀O₄P^(1-)*C₂₅H₃₁N₂O₂RuS⁽¹⁺⁾ / dichloromethane / 10 h / 40 °C / 38002.6 Torr / Autoclave; Glovebox

With 1,3,5-trichloro-2,4,6-triazine; C₁₂H₁₀O₄P^(1-)*C₂₅H₃₁N₂O₂RuS⁽¹⁺⁾; hydrogen; In dichloromethane; toluene;

DOI:10.1002/ejoc.201700236

upstream raw materials:

2,4-bis(4-bromophenyl)-2-methyl-2,3-dihydro-1H-benzo[b][1,4]diazepine

para-bromoacetophenone

1,2-diamino-benzene

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