(2R,3aR,7aR)-N-(benzyloxycarbonyl)-2-methyloctahydroindole-2-carboxylic acid

Base Information

Chemical Name:(2R,3aR,7aR)-N-(benzyloxycarbonyl)-2-methyloctahydroindole-2-carboxylic acid
CAS No.:1316178-05-8
Molecular Formula:C₁₈H₂₃NO₄
Molecular Weight:317.385
Hs Code.:

Synonyms:(2R,3aR,7aR)-N-(benzyloxycarbonyl)-2-methyloctahydroindole-2-carboxylic acid

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Chemical Property of (2R,3aR,7aR)-N-(benzyloxycarbonyl)-2-methyloctahydroindole-2-carboxylic acid

Chemical Property:

Purity/Quality:

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Technology Process of (2R,3aR,7aR)-N-(benzyloxycarbonyl)-2-methyloctahydroindole-2-carboxylic acid

There total 10 articles about (2R,3aR,7aR)-N-(benzyloxycarbonyl)-2-methyloctahydroindole-2-carboxylic acid 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%

: 1316177-99-7
methyl (2R,3aR,7aR)-N-(benzyloxycarbonyl)-2-methyloctahydroindole-2-carboxylate

: 1316178-05-8
(2R,3aR,7aR)-N-(benzyloxycarbonyl)-2-methyloctahydroindole-2-carboxylic acid

Guidance literature:: With potassium hydroxide; In methanol; for 24h; Reflux;
DOI:10.1002/chir.20952

Reference yield:

: methyl (2S*,3aS*,7aS*)-N-(tert-butoxycarbonyl)-2-methyloctahydroindole-2-carboxylate

: 1316178-05-8
(2R,3aR,7aR)-N-(benzyloxycarbonyl)-2-methyloctahydroindole-2-carboxylic acid

Guidance literature:: Multi-step reaction with 4 steps

1: hydrogenchloride / ethyl acetate / 4 h / 20 °C

2: N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C / Cooling with ice

3: Chiralpak^.(R).IC / hexane; tert-butyl methyl ether; chloroform; isopropyl alcohol / Resolution of racemate

4: potassium hydroxide / methanol / 24 h / Reflux

With hydrogenchloride; N-ethyl-N,N-diisopropylamine; potassium hydroxide; In methanol; hexane; dichloromethane; tert-butyl methyl ether; chloroform; ethyl acetate; isopropyl alcohol;
DOI:10.1002/chir.20952

Reference yield:

Indole-2-carboxylic acid: 1477-50-5,1228050-17-6
Indole-2-carboxylic acid

: 1316178-05-8
(2R,3aR,7aR)-N-(benzyloxycarbonyl)-2-methyloctahydroindole-2-carboxylic acid

Guidance literature:: Multi-step reaction with 8 steps

1.1: sulfuric acid / 6 h / Reflux

2.1: dmap / tetrahydrofuran / 2 h / 20 °C

3.1: platinum(IV) oxide; hydrogen; acetic acid / 24 h / 20 °C / 760.05 Torr

4.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere

4.2: -78 - -50 °C / Inert atmosphere

5.1: hydrogenchloride / ethyl acetate / 4 h / 20 °C

6.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C / Cooling with ice

7.1: Chiralpak^.(R).IC / hexane; tert-butyl methyl ether; chloroform; isopropyl alcohol / Resolution of racemate

8.1: potassium hydroxide / methanol / 24 h / Reflux

With hydrogenchloride; dmap; platinum(IV) oxide; sulfuric acid; hydrogen; acetic acid; N-ethyl-N,N-diisopropylamine; potassium hydroxide; lithium diisopropyl amide; In tetrahydrofuran; methanol; hexane; dichloromethane; tert-butyl methyl ether; chloroform; ethyl acetate; isopropyl alcohol;
DOI:10.1002/chir.20952