tert-butyl (S)-5-(benzyloxy)-1-(chloromethyl)-9-methyl-1,2-dihydro-3H-benzo[e]indole-3-carboxylate

Base Information

• Chemical Name: tert-butyl (S)-5-(benzyloxy)-1-(chloromethyl)-9-methyl-1,2-dihydro-3H-benzo[e]indole-3-carboxylate
• CAS No.: 945864-47-1
• Molecular Formula: C₂₆H₂₈ClNO₃
• Molecular Weight: 437.966
• Mol file: 945864-47-1.mol

Synonyms:tert-butyl (S)-5-(benzyloxy)-1-(chloromethyl)-9-methyl-1,2-dihydro-3H-benzo[e]indole-3-carboxylate

Chemical Property of tert-butyl (S)-5-(benzyloxy)-1-(chloromethyl)-9-methyl-1,2-dihydro-3H-benzo[e]indole-3-carboxylate

Chemical Property:

• Boiling Point: 577.4±50.0 °C(Predicted)
• Density: 1.202±0.06 g/cm3(Predicted)

Purity/Quality:

99% ^*data from raw suppliers

Tert-butyl1-(chloromethyl)-9-methyl-5-phenylmethoxy-1,2-dihydrobenzo[e]indole-3-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: (S)-5-(benzyloxy)-1-(chloromethyl)-9-methyl-1,2-dihydro-3H-benzo[e]indole-3-carboxylate is an important organic intermediate to synthetize substituted benzo[e]indole products.

Technology Process of tert-butyl (S)-5-(benzyloxy)-1-(chloromethyl)-9-methyl-1,2-dihydro-3H-benzo[e]indole-3-carboxylate

There total 10 articles about tert-butyl (S)-5-(benzyloxy)-1-(chloromethyl)-9-methyl-1,2-dihydro-3H-benzo[e]indole-3-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: 63.0%

(S)-tert-butyl 5-(benzyloxy)-9-methyl-1-(((methylsulfonyl)oxy)methyl)-1H-benzo[e]indole-3(2H)-carboxylate → tert-butyl (S)-5-(benzyloxy)-1-(chloromethyl)-9-methyl-1,2-dihydro-3H-benzo[e]indole-3-carboxylate (945864-47-1)

Guidance literature:

With lithium chloride; In N,N-dimethyl-formamide; at 80 ℃; for 1.5h;

DOI:10.1021/mp500781a

Reference yield:

tert-butyl (4-(benzyloxy)-8-methylnaphthalen-2-yl)carbamate → tert-butyl (S)-5-(benzyloxy)-1-(chloromethyl)-9-methyl-1,2-dihydro-3H-benzo[e]indole-3-carboxylate (945864-47-1)

Guidance literature:

Multi-step reaction with 5 steps

1.1: N-Bromosuccinimide / tetrahydrofuran / -10 °C

2.1: potassium tert-butylate / tetrahydrofuran / 10 °C

2.2: 3 h / 25 °C

3.1: n-butyllithium / tetrahydrofuran; hexane / 0.17 h / -25 - -20 °C / Inert atmosphere

4.1: triethylamine / dichloromethane / 1.5 h / 0 - 5 °C

5.1: lithium chloride / N,N-dimethyl-formamide / 1.5 h / 80 °C

With N-Bromosuccinimide; n-butyllithium; potassium tert-butylate; triethylamine; lithium chloride; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/mp500781a

Reference yield:

tert-butyl (4-(benzyloxy)-1-bromo-8-methylnaphthalen-2-yl)carbamate → tert-butyl (S)-5-(benzyloxy)-1-(chloromethyl)-9-methyl-1,2-dihydro-3H-benzo[e]indole-3-carboxylate (945864-47-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: potassium tert-butylate / tetrahydrofuran / 10 °C

1.2: 3 h / 25 °C

2.1: n-butyllithium / tetrahydrofuran; hexane / 0.17 h / -25 - -20 °C / Inert atmosphere

3.1: triethylamine / dichloromethane / 1.5 h / 0 - 5 °C

4.1: lithium chloride / N,N-dimethyl-formamide / 1.5 h / 80 °C

With n-butyllithium; potassium tert-butylate; triethylamine; lithium chloride; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/mp500781a

upstream raw materials:

methyl 4-hydroxy-8-methyl-2-naphthoate

benzyl chloride

Downstream raw materials:

(S)-N-(2-(1-(chloromethyl)-5-hydroxy-9-methyl-2,3-dihydro-1H-benzo[e]indole-3-carbonyl)-imidazo[1,2-a]pyridin-6-yl)-4-(methoxymethoxy)benzamide