1,1-dimethylethyl (4R,5S)-[1,3,4,5-tetrahydro-5-[((2RS)-2-methyl-1-propanol)-3-yl]-1-[(4-methylphenyl)sulfonyl]benz[cd]indol-4-yl]-N-methylcarbamate

Base Information

• Chemical Name: 1,1-dimethylethyl (4R,5S)-[1,3,4,5-tetrahydro-5-[((2RS)-2-methyl-1-propanol)-3-yl]-1-[(4-methylphenyl)sulfonyl]benz[cd]indol-4-yl]-N-methylcarbamate
• CAS No.: 254736-53-3
• Molecular Formula: C₂₈H₃₆N₂O₅S
• Molecular Weight: 512.67
• Mol file: 254736-53-3.mol

Synonyms:1,1-dimethylethyl (4R,5S)-[1,3,4,5-tetrahydro-5-[((2RS)-2-methyl-1-propanol)-3-yl]-1-[(4-methylphenyl)sulfonyl]benz[cd]indol-4-yl]-N-methylcarbamate

Chemical Property of 1,1-dimethylethyl (4R,5S)-[1,3,4,5-tetrahydro-5-[((2RS)-2-methyl-1-propanol)-3-yl]-1-[(4-methylphenyl)sulfonyl]benz[cd]indol-4-yl]-N-methylcarbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,1-dimethylethyl (4R,5S)-[1,3,4,5-tetrahydro-5-[((2RS)-2-methyl-1-propanol)-3-yl]-1-[(4-methylphenyl)sulfonyl]benz[cd]indol-4-yl]-N-methylcarbamate

There total 5 articles about 1,1-dimethylethyl (4R,5S)-[1,3,4,5-tetrahydro-5-[((2RS)-2-methyl-1-propanol)-3-yl]-1-[(4-methylphenyl)sulfonyl]benz[cd]indol-4-yl]-N-methylcarbamate 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: 90.0%

1,1-dimethylethyl (4R,5S)-[1,3,4,5-tetrahydro-5-(2-methyl-1-propenyl)-1-[(4-methylphenyl)sulfonyl]benz[cd]indol-4-yl]-N-methylcarbamate (254736-52-2) → 1,1-dimethylethyl (4R,5S)-[1,3,4,5-tetrahydro-5-[((2RS)-2-methyl-1-propanol)-3-yl]-1-[(4-methylphenyl)sulfonyl]benz[cd]indol-4-yl]-N-methylcarbamate (254736-53-3)

Guidance literature:

1,1-dimethylethyl (4R,5S)-[1,3,4,5-tetrahydro-5-(2-methyl-1-propenyl)-1-[(4-methylphenyl)sulfonyl]benz[cd]indol-4-yl]-N-methylcarbamate; With borane-THF; In tetrahydrofuran; at 0 ℃; for 0.5h;

With sodium hydroxide; dihydrogen peroxide; at 20 ℃; for 1h;

DOI:10.1248/cpb.47.1587

Reference yield:

methyl [4R-(Z)]-[4-[[(1,1-dimethylethoxy)carbonyl]methylamino]-3,4-dihydro-1-[(4-methylphenyl)sulfonyl]benz[cd]indol-5(1H)-ylidene]acetate → 1,1-dimethylethyl (4R,5S)-[1,3,4,5-tetrahydro-5-[((2RS)-2-methyl-1-propanol)-3-yl]-1-[(4-methylphenyl)sulfonyl]benz[cd]indol-4-yl]-N-methylcarbamate (254736-53-3)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 95 percent / H₂ / 10 percent Pd/C / methanol / 0.5 h

2.1: pyridine / toluene; tetrahydrofuran / 0.5 h / -20 °C

3.1: aq. HCl / toluene; tetrahydrofuran; ethyl acetate

4.1: 84 percent / pyridine / toluene; tetrahydrofuran / 0.5 h / -20 °C

5.1: BH₃*THF / tetrahydrofuran / 0.5 h / 0 °C

5.2: 90 percent / aq. H₂O₂; NaOH / 1 h / 20 °C

With pyridine; hydrogenchloride; borane-THF; hydrogen; palladium on activated charcoal; In tetrahydrofuran; methanol; ethyl acetate; toluene; 1.1: Catalytic hydrogenation / 2.1: Condensation / 3.1: Hydrolysis / 4.1: Substitution / 5.1: hydroboration / 5.2: Oxidation;

DOI:10.1248/cpb.47.1587

Reference yield:

methyl (4R,5S)-4-[[(1,1-dimethylethoxy)carbonyl]methylamino]-1,3,4,5-tetrahydro-1-[(4-methylphenyl)sulfonyl]benz[cd]indol-5-acetate (186084-75-3) → 1,1-dimethylethyl (4R,5S)-[1,3,4,5-tetrahydro-5-[((2RS)-2-methyl-1-propanol)-3-yl]-1-[(4-methylphenyl)sulfonyl]benz[cd]indol-4-yl]-N-methylcarbamate (254736-53-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: pyridine / toluene; tetrahydrofuran / 0.5 h / -20 °C

2.1: aq. HCl / toluene; tetrahydrofuran; ethyl acetate

3.1: 84 percent / pyridine / toluene; tetrahydrofuran / 0.5 h / -20 °C

4.1: BH₃*THF / tetrahydrofuran / 0.5 h / 0 °C

4.2: 90 percent / aq. H₂O₂; NaOH / 1 h / 20 °C

With pyridine; hydrogenchloride; borane-THF; In tetrahydrofuran; ethyl acetate; toluene; 1.1: Condensation / 2.1: Hydrolysis / 3.1: Substitution / 4.1: hydroboration / 4.2: Oxidation;

DOI:10.1248/cpb.47.1587

upstream raw materials:

1,1-dimethylethyl (4R,5S)-[1,3,4,5-tetrahydro-5-(2-methyl-1-propenyl)-1-[(4-methylphenyl)sulfonyl]benz[cd]indol-4-yl]-N-methylcarbamate

methyl (4R,5S)-4-[[(1,1-dimethylethoxy)carbonyl]methylamino]-1,3,4,5-tetrahydro-1-[(4-methylphenyl)sulfonyl]benz[cd]indol-5-acetate

1,1-dimethylethyl (4R,5S)-[1,3,4,5-tetrahydro-5-(2-oxopropyl)-1-[(4-methylphenyl)sulfonyl]benz[cd]indol-4-yl]-N-methylcarbamate

Downstream raw materials:

(+)-Costaclavine

(5R,8R,10R)-1-(4-methylphenyl)sulfonyl-6,8-dimethylergoline

(5R,8S,10R)-1-(4-methylphenyl)sulfonyl-6,8-dimethylergoline