(2R,3aS,8aR)-2-ethyl-2,3,3a,8a-tetrahydro-pyrrolo[2,3-b]indole-1,2,8-tricarboxylic acid 2-allyl ester 1,8-dibenzyl ester

Base Information

Chemical Name:(2R,3aS,8aR)-2-ethyl-2,3,3a,8a-tetrahydro-pyrrolo[2,3-b]indole-1,2,8-tricarboxylic acid 2-allyl ester 1,8-dibenzyl ester
CAS No.:354117-21-8
Molecular Formula:C₃₂H₃₂N₂O₆
Molecular Weight:540.616
Hs Code.:

Synonyms:(2R,3aS,8aR)-2-ethyl-2,3,3a,8a-tetrahydro-pyrrolo[2,3-b]indole-1,2,8-tricarboxylic acid 2-allyl ester 1,8-dibenzyl ester

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Chemical Property of (2R,3aS,8aR)-2-ethyl-2,3,3a,8a-tetrahydro-pyrrolo[2,3-b]indole-1,2,8-tricarboxylic acid 2-allyl ester 1,8-dibenzyl ester

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Technology Process of (2R,3aS,8aR)-2-ethyl-2,3,3a,8a-tetrahydro-pyrrolo[2,3-b]indole-1,2,8-tricarboxylic acid 2-allyl ester 1,8-dibenzyl ester

There total 5 articles about (2R,3aS,8aR)-2-ethyl-2,3,3a,8a-tetrahydro-pyrrolo[2,3-b]indole-1,2,8-tricarboxylic acid 2-allyl ester 1,8-dibenzyl 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: 79.0%

: 75-03-6
ethyl iodide

: 354117-19-4
(2R,3aS,8aS)-3,3a,8,8a-tetrahydro-2H-pyrrolo[2,3-b]indole-1,2-dicarboxylic acid 2-allyl ester 1-benzyl ester

: 354117-21-8
(2R,3aS,8aR)-2-ethyl-2,3,3a,8a-tetrahydro-pyrrolo[2,3-b]indole-1,2,8-tricarboxylic acid 2-allyl ester 1,8-dibenzyl ester

Guidance literature:: (2R,3aS,8aS)-3,3a,8,8a-tetrahydro-2H-pyrrolo[2,3-b]indole-1,2-dicarboxylic acid 2-allyl ester 1-benzyl ester; With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 2h;

ethyl iodide; In tetrahydrofuran; at -78 - 20 ℃; Further stages.;
DOI:10.1021/jm010825z

Reference yield:

: 501-53-1,94274-21-2
benzyl chloroformate

: 354117-21-8
(2R,3aS,8aR)-2-ethyl-2,3,3a,8a-tetrahydro-pyrrolo[2,3-b]indole-1,2,8-tricarboxylic acid 2-allyl ester 1,8-dibenzyl ester

Guidance literature:: Multi-step reaction with 2 steps

1.1: 86 percent / aq. Na₂CO₃ / dioxane / 16 h / 20 °C

2.1: LHMDS; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone / tetrahydrofuran / 2 h / -78 °C

2.2: 79 percent / tetrahydrofuran / -78 - 20 °C

With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; sodium carbonate; lithium hexamethyldisilazane; In tetrahydrofuran; 1,4-dioxane;
DOI:10.1021/jm010825z

Reference yield:

: 354117-18-3
(2R,3aS,8aS)-3,3a,8,8a-tetrahydro-2H-pyrrolo[2,3-b]indole-1,2-dicarboxylic acid 2-allyl ester 1-benzyl ester

: 354117-21-8
(2R,3aS,8aR)-2-ethyl-2,3,3a,8a-tetrahydro-pyrrolo[2,3-b]indole-1,2,8-tricarboxylic acid 2-allyl ester 1,8-dibenzyl ester

Guidance literature:: Multi-step reaction with 2 steps

1.1: 86 percent / aq. Na₂CO₃ / dioxane / 16 h / 20 °C

2.1: LHMDS; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone / tetrahydrofuran / 2 h / -78 °C

2.2: 79 percent / tetrahydrofuran / -78 - 20 °C

With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; sodium carbonate; lithium hexamethyldisilazane; In tetrahydrofuran; 1,4-dioxane;
DOI:10.1021/jm010825z