(1R,3aS,8bR)-dimethyl 4-(tert-butyldimethylsilyl)-1-(4-methoxy phenyl)-8b-methyl-1,3a,4,8b-tetrahydro cyclopenta[b]indole-3,3(2H)-dicarboxylate

Base Information

• Chemical Name: (1R,3aS,8bR)-dimethyl 4-(tert-butyldimethylsilyl)-1-(4-methoxy phenyl)-8b-methyl-1,3a,4,8b-tetrahydro cyclopenta[b]indole-3,3(2H)-dicarboxylate
• CAS No.: 1432791-31-5
• Molecular Formula: C₂₉H₃₉NO₅Si
• Molecular Weight: 509.718
• Mol file: 1432791-31-5.mol

Synonyms:

Chemical Property of (1R,3aS,8bR)-dimethyl 4-(tert-butyldimethylsilyl)-1-(4-methoxy phenyl)-8b-methyl-1,3a,4,8b-tetrahydro cyclopenta[b]indole-3,3(2H)-dicarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,3aS,8bR)-dimethyl 4-(tert-butyldimethylsilyl)-1-(4-methoxy phenyl)-8b-methyl-1,3a,4,8b-tetrahydro cyclopenta[b]indole-3,3(2H)-dicarboxylate

There total 4 articles about (1R,3aS,8bR)-dimethyl 4-(tert-butyldimethylsilyl)-1-(4-methoxy phenyl)-8b-methyl-1,3a,4,8b-tetrahydro cyclopenta[b]indole-3,3(2H)-dicarboxylate 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:

dimethyl 2-(4-methoxyphenyl)cyclopropane-1,1-dicarboxylate (75073-97-1) + 1-(tert-Butyldimethylsilyl)-3-methylindole (108939-97-5) → (1R,3aS,8bR)-dimethyl 4-(tert-butyldimethylsilyl)-1-(4-methoxy phenyl)-8b-methyl-1,3a,4,8b-tetrahydro cyclopenta[b]indole-3,3(2H)-dicarboxylate (1432791-31-5) + (1R,3aR,8bS)-dimethyl 4-(tert-butyldimethylsilyl)-1-(4-methoxy phenyl)-8b-methyl-1,3a,4,8b-tetrahydro cyclopenta[b]indole-3,3(2H)-dicarboxylate (1432791-32-6)

Guidance literature:

With ytterbium(III) triflate; In acetonitrile; at 20 - 40 ℃; for 2.75h; Overall yield = 49 %; Overall yield = 44.1 mg; Inert atmosphere; Molecular sieve; Glovebox;

DOI:10.1021/ol4010646

Reference yield:

indole (120-72-9) → (1R,3aS,8bR)-dimethyl 4-(tert-butyldimethylsilyl)-1-(4-methoxy phenyl)-8b-methyl-1,3a,4,8b-tetrahydro cyclopenta[b]indole-3,3(2H)-dicarboxylate (1432791-31-5) + C29H39NO5Si + (1R,3aR,8bS)-dimethyl 4-(tert-butyldimethylsilyl)-1-(4-methoxy phenyl)-8b-methyl-1,3a,4,8b-tetrahydro cyclopenta[b]indole-3,3(2H)-dicarboxylate (1432791-32-6) + C29H39NO5Si

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydride / tetrahydrofuran / 1.25 h / 0 - 20 °C / Inert atmosphere

1.2: 20 °C / Inert atmosphere

2.1: magnesium iodide; (4S,4'S)-2,2'-(4-bromopyridine-2,6-diyl)bis(4-tert-butyl-4,5-dihydrooxazole); tetrachloromethane / 20 °C / Inert atmosphere; Molecular sieve; Glovebox

With tetrachloromethane; (4S,4'S)-2,2'-(4-bromopyridine-2,6-diyl)bis(4-tert-butyl-4,5-dihydrooxazole); sodium hydride; magnesium iodide; In tetrahydrofuran; 2.1: |Friedel-Crafts Alkylation;

DOI:10.1021/ol4010646

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → (1R,3aS,8bR)-dimethyl 4-(tert-butyldimethylsilyl)-1-(4-methoxy phenyl)-8b-methyl-1,3a,4,8b-tetrahydro cyclopenta[b]indole-3,3(2H)-dicarboxylate (1432791-31-5) + C29H39NO5Si + (1R,3aR,8bS)-dimethyl 4-(tert-butyldimethylsilyl)-1-(4-methoxy phenyl)-8b-methyl-1,3a,4,8b-tetrahydro cyclopenta[b]indole-3,3(2H)-dicarboxylate (1432791-32-6) + C29H39NO5Si

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydride / tetrahydrofuran / 1.25 h / 0 - 20 °C / Inert atmosphere

1.2: 20 °C / Inert atmosphere

2.1: magnesium iodide; (4S,4'S)-2,2'-(4-bromopyridine-2,6-diyl)bis(4-tert-butyl-4,5-dihydrooxazole); tetrachloromethane / 20 °C / Inert atmosphere; Molecular sieve; Glovebox

With tetrachloromethane; (4S,4'S)-2,2'-(4-bromopyridine-2,6-diyl)bis(4-tert-butyl-4,5-dihydrooxazole); sodium hydride; magnesium iodide; In tetrahydrofuran; 2.1: |Friedel-Crafts Alkylation;

DOI:10.1021/ol4010646

upstream raw materials:

dimethyl 2-(4-methoxyphenyl)cyclopropane-1,1-dicarboxylate

1-(tert-Butyldimethylsilyl)-3-methylindole

N-tert-butyldimethylsilylindole

indole

Refernces