methyl 5-methyl-9-oxo-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctaindole-8-carboxylate

Base Information

• Chemical Name: methyl 5-methyl-9-oxo-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctaindole-8-carboxylate
• CAS No.: 2738-25-2
• Molecular Formula: C₂₄H₂₄N₂O₃
• Molecular Weight: 388.466

Synonyms:methyl 5-methyl-9-oxo-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctaindole-8-carboxylate

Chemical Property of methyl 5-methyl-9-oxo-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctaindole-8-carboxylate

Chemical Property:

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Technology Process of methyl 5-methyl-9-oxo-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctaindole-8-carboxylate

There total 29 articles about methyl 5-methyl-9-oxo-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctaindole-8-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: 92.0%

methyl trans-2-benzyl-3-methoxycarbonyl-9-methyl-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole-1-propionate (4837-57-4,19171-89-2,47679-01-6,84129-60-2,91279-02-6,120056-44-2,141847-51-0,142292-54-4) → methyl 5-methyl-9-oxo-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctaindole-8-carboxylate (2738-25-2,123806-88-2,123806-89-3)

Guidance literature:

With methanol; sodium hydride; In toluene; 1) reflux, 6 h, 2) r.t., 12 h;

DOI:10.1016/S0040-4020(01)88507-0

Reference yield: 85.3%

methyl 2-benzyl-3-(methoxycarbonyl)-9-methyl-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole-1-propionate (19171-89-2) → methyl 5-methyl-9-oxo-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctaindole-8-carboxylate (2738-25-2)

Guidance literature:

With sodium hydride; In methanol; toluene; for 2h; Heating;

DOI:10.1021/ja00342a045

Reference yield:

benzaldehyde (100-52-7) → methyl 5-methyl-9-oxo-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctaindole-8-carboxylate (2738-25-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 2.) sodium borohydride / 1.) methanol, 6 h, 2.) 0-5 deg C, 4 h

2: 97 percent / benzene; dioxane / 20 h / Heating

3: 91 percent / HCl / 2.5 h / Heating

4: 85.3 percent / NaH / toluene; methanol / 2 h / Heating

With hydrogenchloride; sodium tetrahydroborate; sodium hydride; In 1,4-dioxane; methanol; toluene; benzene;

DOI:10.1021/ja00342a045

upstream raw materials:

methyl 2-benzyl-3-(methoxycarbonyl)-9-methyl-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole-1-propionate

benzaldehyde

N_a-methyl tryptophan methyl ester

(+/-)-N_a-methyl-N_b-benzyltriptophan methyl ester

Downstream raw materials:

(6S,10S)-(-)-5-methyl-9-oxo-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctaindole

5-methyl-9-hydroxy-9α-chloro-phenylsulfinylmethyl-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctindole

2'-phenylsulfinyl-5-methyl-12-benzyl-6,7,8,9,10,11-hexahydro-oxirano-spiro<2',9>-6,10-imino-5H-cyclooctindole

5-methyl-9-butyryloxymethyl-12-benzyl-6,7,10,11-tetrahydro-6,10-imino-5H-cyclooctindole

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