3-cyclohexyl-2-{2-[(2S)-oxiran-2-ylmethoxy]phenyl}-1H-indole-6-carboxylic acid methyl ester

Base Information

• Chemical Name: 3-cyclohexyl-2-{2-[(2S)-oxiran-2-ylmethoxy]phenyl}-1H-indole-6-carboxylic acid methyl ester
• CAS No.: 886041-53-8
• Molecular Formula: C₂₅H₂₇NO₄
• Molecular Weight: 405.494

Synonyms:3-cyclohexyl-2-{2-[(2S)-oxiran-2-ylmethoxy]phenyl}-1H-indole-6-carboxylic acid methyl ester

Chemical Property of 3-cyclohexyl-2-{2-[(2S)-oxiran-2-ylmethoxy]phenyl}-1H-indole-6-carboxylic acid methyl ester

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Technology Process of 3-cyclohexyl-2-{2-[(2S)-oxiran-2-ylmethoxy]phenyl}-1H-indole-6-carboxylic acid methyl ester

There total 5 articles about 3-cyclohexyl-2-{2-[(2S)-oxiran-2-ylmethoxy]phenyl}-1H-indole-6-carboxylic acid methyl ester 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: 82.0%

3-cyclohexyl-2-(2-hydroxy-phenyl)-1H-indole-6-carboxylic acid methyl ester (863578-50-1) + S-oxiran-2-ylmethyl 4-nitrobenzenesulfonate (118712-60-0,118629-64-4) → 3-cyclohexyl-2-{2-[(2S)-oxiran-2-ylmethoxy]phenyl}-1H-indole-6-carboxylic acid methyl ester (886041-53-8)

Guidance literature:

With cesium fluoride; In N,N-dimethyl-formamide;

DOI:10.1055/s-0030-1260790

Reference yield: 76.0%

3-cyclohexyl-2-(2-hydroxy-phenyl)-1H-indole-6-carboxylic acid methyl ester (863578-50-1) + (S)-Glycidyl tosylate (70987-78-9,6746-81-2) → 3-cyclohexyl-2-{2-[(2S)-oxiran-2-ylmethoxy]phenyl}-1H-indole-6-carboxylic acid methyl ester (886041-53-8)

Guidance literature:

3-cyclohexyl-2-(2-hydroxy-phenyl)-1H-indole-6-carboxylic acid methyl ester; With potassium tert-butylate; In N,N-dimethyl acetamide; at 20 - 25 ℃; Large scale reaction;

(S)-Glycidyl tosylate; In N,N-dimethyl acetamide; at 65 ℃; for 2.5h; Large scale reaction;

DOI:10.1021/op200002u

Reference yield: 74.0%

3-cyclohexyl-2-(2-hydroxy-phenyl)-1H-indole-6-carboxylic acid methyl ester (863578-50-1) + (2s)-(+)-glycidyl 3-nitrobenzenesulfonate (115314-14-2) → 3-cyclohexyl-2-{2-[(2S)-oxiran-2-ylmethoxy]phenyl}-1H-indole-6-carboxylic acid methyl ester (886041-53-8)

Guidance literature:

With cesium fluoride; In N,N-dimethyl-formamide; at 20 ℃;

upstream raw materials:

3-cyclohexyl-2-(2-hydroxy-phenyl)-1H-indole-6-carboxylic acid methyl ester

(2s)-(+)-glycidyl 3-nitrobenzenesulfonate

methyl 2-bromo-3-cyclohexyl-1H-indole-6-carboxylate

2-hydroxyphenyl boronic acid

Downstream raw materials:

methyl 14-cyclohexyl-7-[methyl(2-pyrrolidin-1-ylethyl)amino]-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate

methyl 14-cyclohexyl-7-{[2-(dimethylamino)ethyl]amino}-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate

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