ethyl 2-(N-tert-butoxycarbonyl-N-methylamino)methyl-3-hydroxy-3-(1-benzoyl-1,2,2a,3-tetrahydrobenzindol-5-yl)propionate

Base Information

• Chemical Name: ethyl 2-(N-tert-butoxycarbonyl-N-methylamino)methyl-3-hydroxy-3-(1-benzoyl-1,2,2a,3-tetrahydrobenzindol-5-yl)propionate
• CAS No.: 107206-02-0
• Molecular Formula: C₃₀H₃₆N₂O₆
• Molecular Weight: 520.626
• Mol file: 107206-02-0.mol

Synonyms:ethyl 2-(N-tert-butoxycarbonyl-N-methylamino)methyl-3-hydroxy-3-(1-benzoyl-1,2,2a,3-tetrahydrobenzindol-5-yl)propionate

Chemical Property of ethyl 2-(N-tert-butoxycarbonyl-N-methylamino)methyl-3-hydroxy-3-(1-benzoyl-1,2,2a,3-tetrahydrobenzindol-5-yl)propionate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl 2-(N-tert-butoxycarbonyl-N-methylamino)methyl-3-hydroxy-3-(1-benzoyl-1,2,2a,3-tetrahydrobenzindol-5-yl)propionate

There total 8 articles about ethyl 2-(N-tert-butoxycarbonyl-N-methylamino)methyl-3-hydroxy-3-(1-benzoyl-1,2,2a,3-tetrahydrobenzindol-5-yl)propionate 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: 99.0%

Ethyl 3-propionate (54424-07-6) + 1-benzoyl-1,2,2a,3-tetrahydrobenzindole-5-carbaldehyde → ethyl 2-(N-tert-butoxycarbonyl-N-methylamino)methyl-3-hydroxy-3-(1-benzoyl-1,2,2a,3-tetrahydrobenzindol-5-yl)propionate (107206-02-0)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; for 0.5h;

DOI:10.1248/cpb.35.4793

Reference yield: 99.0%

Ethyl 3-propionate (54424-07-6) + 1-benzoyl-1,2,2a,3-tetrahydro-benz[cd]indole-5-carbaldehyde (62592-64-7) → ethyl 2-(N-tert-butoxycarbonyl-N-methylamino)methyl-3-hydroxy-3-(1-benzoyl-1,2,2a,3-tetrahydrobenzindol-5-yl)propionate (107206-02-0)

Guidance literature:

DOI:10.1248/cpb.34.442

Reference yield:

1-benzoyl-1,2,2a,3-tetrahydrobenzindole-5-carbonyl chloride (107183-50-6) → ethyl 2-(N-tert-butoxycarbonyl-N-methylamino)methyl-3-hydroxy-3-(1-benzoyl-1,2,2a,3-tetrahydrobenzindol-5-yl)propionate (107206-02-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 54 percent / H₂ / 10percent Pd-BaSO₄ / ethyl acetate; xylene / 2 h / 90 - 100 °C

2: 99 percent / LDA / tetrahydrofuran / 0.5 h / -78 °C

With hydrogen; lithium diisopropyl amide; palladium on barium sulfate; In tetrahydrofuran; ethyl acetate; xylene;

DOI:10.1248/cpb.35.4793

upstream raw materials:

Ethyl 3-propionate

1-benzoyl-1,2,2a,3-tetrahydro-benz[cd]indole-5-carbaldehyde

1-benzoyl-2,2a,3,4-tetrahydro-1H-benz[cd]indol-5-one

1-benzoyl-1,2,2a,3-tetrahydrobenzindole-5-carbonitrile

Downstream raw materials:

(5aS,6aR,9S)-4-Benzoyl-7-methyl-4,5,5a,6,6a,7,8,9-octahydro-indolo[4,3-fg]quinoline-9-carboxylic acid ethyl ester

1-benzoyl-8-ethoxycarbonyl-2,3-dihydro-6-methyl-Δ^8,9-ergoline

3-(1-Benzoyl-1,2,2a,3-tetrahydro-benzo[cd]indol-5-yl)-2-[(tert-butoxycarbonyl-methyl-amino)-methyl]-3-chloro-propionic acid ethyl ester

3-(1-Benzoyl-1,2,2a,3-tetrahydro-benzo[cd]indol-5-yl)-2-[(tert-butoxycarbonyl-methyl-amino)-methyl]-3-methanesulfonyloxy-propionic acid ethyl ester