ethyl 2-(N-tert-butoxyvarbonyl-N-methylamino)methyl-3-(1-benzoyl-1,2,2a,3-tetrahydrobenzindol-5-yl)propenoate

Base Information

Chemical Name:ethyl 2-(N-tert-butoxyvarbonyl-N-methylamino)methyl-3-(1-benzoyl-1,2,2a,3-tetrahydrobenzindol-5-yl)propenoate
CAS No.:117138-59-7
Molecular Formula:C₃₀H₃₄N₂O₅
Molecular Weight:502.61
Hs Code.:

ethyl 2-(N-tert-butoxyvarbonyl-N-methylamino)methyl-3-(1-benzoyl-1,2,2a,3-tetrahydrobenz<cd>indol-5-yl)propenoate

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

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

There total 10 articles about ethyl 2-(N-tert-butoxyvarbonyl-N-methylamino)methyl-3-(1-benzoyl-1,2,2a,3-tetrahydrobenzindol-5-yl)propenoate 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: 18.0%

: 107206-03-1
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

: 117138-59-7
ethyl 2-(N-tert-butoxyvarbonyl-N-methylamino)methyl-3-(1-benzoyl-1,2,2a,3-tetrahydrobenzindol-5-yl)propenoate

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dimethyl sulfoxide; for 0.0833333h; Ambient temperature;
DOI:10.1248/cpb.35.4793

Reference yield:

: 107183-50-6
1-benzoyl-1,2,2a,3-tetrahydrobenzindole-5-carbonyl chloride

: 117138-59-7
ethyl 2-(N-tert-butoxyvarbonyl-N-methylamino)methyl-3-(1-benzoyl-1,2,2a,3-tetrahydrobenzindol-5-yl)propenoate

Guidance literature:: Multi-step reaction with 4 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

3: TEA / CH₂Cl₂ / 0.25 h / Ambient temperature

4: 18 percent / DBU / dimethylsulfoxide / 0.08 h / Ambient temperature

With TEA; hydrogen; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium diisopropyl amide; palladium on barium sulfate; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; ethyl acetate; xylene;
DOI:10.1248/cpb.35.4793

Reference yield:

: 1,2,2a,3-tetrahydrobenzindole-5-carboxylic acid

: 117138-59-7
ethyl 2-(N-tert-butoxyvarbonyl-N-methylamino)methyl-3-(1-benzoyl-1,2,2a,3-tetrahydrobenzindol-5-yl)propenoate

Guidance literature:: Multi-step reaction with 6 steps

1: 80 percent / 0.2N NaOH / 1 h / Ambient temperature

2: 100 percent / SOCl₂ / benzene / 2.5 h / 95 °C

3: 54 percent / H₂ / 10percent Pd-BaSO₄ / ethyl acetate; xylene / 2 h / 90 - 100 °C

4: 99 percent / LDA / tetrahydrofuran / 0.5 h / -78 °C

5: TEA / CH₂Cl₂ / 0.25 h / Ambient temperature

6: 18 percent / DBU / dimethylsulfoxide / 0.08 h / Ambient temperature

With sodium hydroxide; thionyl chloride; TEA; hydrogen; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium diisopropyl amide; palladium on barium sulfate; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; ethyl acetate; xylene; benzene;
DOI:10.1248/cpb.35.4793