(-)-(4aS,9aR)-methyl 6-phenyl-trans-2,3,4,4a-tetrahydro-1H-carbazole-9-(9aH)-carboxylate

Base Information

• Chemical Name: (-)-(4aS,9aR)-methyl 6-phenyl-trans-2,3,4,4a-tetrahydro-1H-carbazole-9-(9aH)-carboxylate
• CAS No.: 1333386-02-9
• Molecular Formula: C₂₀H₂₁NO₂
• Molecular Weight: 307.392
• Mol file: 1333386-02-9.mol

Synonyms:(-)-(4aS,9aR)-methyl 6-phenyl-trans-2,3,4,4a-tetrahydro-1H-carbazole-9-(9aH)-carboxylate

Chemical Property of (-)-(4aS,9aR)-methyl 6-phenyl-trans-2,3,4,4a-tetrahydro-1H-carbazole-9-(9aH)-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-(4aS,9aR)-methyl 6-phenyl-trans-2,3,4,4a-tetrahydro-1H-carbazole-9-(9aH)-carboxylate

There total 5 articles about (-)-(4aS,9aR)-methyl 6-phenyl-trans-2,3,4,4a-tetrahydro-1H-carbazole-9-(9aH)-carboxylate 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: 88.0%

methyl (3-bromo-[1,1'-biphenyl]-4-yl)(cyclohexyl)carbamate (1333385-84-4) → (-)-(4aS,9aR)-methyl 6-phenyl-trans-2,3,4,4a-tetrahydro-1H-carbazole-9-(9aH)-carboxylate (1333386-02-9)

Guidance literature:

With [{Pd(cinnamyl)(μ-Cl)}₂]; (S,S)-1,3-bis(2,2-dimethyl-1-naphthylpropyl)imidazolium iodide; caesium carbonate; cesium pivalate; In 1,3,5-trimethyl-benzene; at 160 ℃; for 3h; optical yield given as %ee; Inert atmosphere;

DOI:10.1002/anie.201102639

Reference yield:

C18H18BrN → (-)-(4aS,9aR)-methyl 6-phenyl-trans-2,3,4,4a-tetrahydro-1H-carbazole-9-(9aH)-carboxylate (1333386-02-9)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium tetrahydroborate / methanol / 4 h / Inert atmosphere

2: 4 h / Reflux

3: (S,S)-1,3-bis(2,2-dimethyl-1-naphthylpropyl)imidazolium iodide; [{Pd(cinnamyl)(μ-Cl)}₂]; caesium carbonate; cesium pivalate / 1,3,5-trimethyl-benzene / 3 h / 160 °C / Inert atmosphere

With sodium tetrahydroborate; [{Pd(cinnamyl)(μ-Cl)}₂]; (S,S)-1,3-bis(2,2-dimethyl-1-naphthylpropyl)imidazolium iodide; caesium carbonate; cesium pivalate; In methanol; 1,3,5-trimethyl-benzene;

DOI:10.1002/anie.201102639

Reference yield:

3-bromo-[1,1'-biphenyl]-4-amine (41738-70-9) → (-)-(4aS,9aR)-methyl 6-phenyl-trans-2,3,4,4a-tetrahydro-1H-carbazole-9-(9aH)-carboxylate (1333386-02-9)

Guidance literature:

Multi-step reaction with 4 steps

1: benzene / 96 h / Molecular sieve; Reflux

2: sodium tetrahydroborate / methanol / 4 h / Inert atmosphere

3: 4 h / Reflux

4: (S,S)-1,3-bis(2,2-dimethyl-1-naphthylpropyl)imidazolium iodide; [{Pd(cinnamyl)(μ-Cl)}₂]; caesium carbonate; cesium pivalate / 1,3,5-trimethyl-benzene / 3 h / 160 °C / Inert atmosphere

With sodium tetrahydroborate; [{Pd(cinnamyl)(μ-Cl)}₂]; (S,S)-1,3-bis(2,2-dimethyl-1-naphthylpropyl)imidazolium iodide; caesium carbonate; cesium pivalate; In methanol; 1,3,5-trimethyl-benzene; benzene;

DOI:10.1002/anie.201102639

upstream raw materials:

methyl (3-bromo-[1,1'-biphenyl]-4-yl)(cyclohexyl)carbamate

3-bromo-[1,1'-biphenyl]-4-amine

cyclohexanone