methyl (2S,3aS,7aS)-N-(benzyloxycarbonyl)-2-methyloctahydroindole-2-carboxylate

Base Information

Chemical Name:methyl (2S,3aS,7aS)-N-(benzyloxycarbonyl)-2-methyloctahydroindole-2-carboxylate
CAS No.:1316177-96-4
Molecular Formula:C₁₉H₂₅NO₄
Molecular Weight:331.412
Hs Code.:

Synonyms:methyl (2S,3aS,7aS)-N-(benzyloxycarbonyl)-2-methyloctahydroindole-2-carboxylate

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Chemical Property of methyl (2S,3aS,7aS)-N-(benzyloxycarbonyl)-2-methyloctahydroindole-2-carboxylate

Chemical Property:

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Technology Process of methyl (2S,3aS,7aS)-N-(benzyloxycarbonyl)-2-methyloctahydroindole-2-carboxylate

There total 9 articles about methyl (2S,3aS,7aS)-N-(benzyloxycarbonyl)-2-methyloctahydroindole-2-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:

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

: 1316177-96-4
methyl (2S,3aS,7aS)-N-(benzyloxycarbonyl)-2-methyloctahydroindole-2-carboxylate

Guidance literature:: Multi-step reaction with 7 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

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

Reference yield:

: methyl (2S*,3aS*,7aS*)-2-methyloctahydroindole-2-carboxylate hydrochloride

: 1316177-96-4
methyl (2S,3aS,7aS)-N-(benzyloxycarbonyl)-2-methyloctahydroindole-2-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

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

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

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

Reference yield:

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

: 1316177-96-4
methyl (2S,3aS,7aS)-N-(benzyloxycarbonyl)-2-methyloctahydroindole-2-carboxylate

Guidance literature:: Multi-step reaction with 3 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

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