3a-benzyl-1-methyl-2,3,3a,8a-tetrahydro-1H-pyrrolo[2,3-b]indole-8-carboxylic acid tert-butyl ester

Base Information

Chemical Name:3a-benzyl-1-methyl-2,3,3a,8a-tetrahydro-1H-pyrrolo[2,3-b]indole-8-carboxylic acid tert-butyl ester
CAS No.:799561-68-5
Molecular Formula:C₂₃H₂₈N₂O₂
Molecular Weight:364.488
Hs Code.:

3a-benzyl-1-methyl-2,3,3a,8a-tetrahydro-1<i>H</i>-pyrrolo[2,3-<i>b</i>]indole-8-carboxylic acid <i>tert</i>-butyl ester

Synonyms:3a-benzyl-1-methyl-2,3,3a,8a-tetrahydro-1H-pyrrolo[2,3-b]indole-8-carboxylic acid tert-butyl ester

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Chemical Property of 3a-benzyl-1-methyl-2,3,3a,8a-tetrahydro-1H-pyrrolo[2,3-b]indole-8-carboxylic acid tert-butyl ester

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Technology Process of 3a-benzyl-1-methyl-2,3,3a,8a-tetrahydro-1H-pyrrolo[2,3-b]indole-8-carboxylic acid tert-butyl ester

There total 4 articles about 3a-benzyl-1-methyl-2,3,3a,8a-tetrahydro-1H-pyrrolo[2,3-b]indole-8-carboxylic acid tert-butyl 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%

: 24424-99-5
di-tert-butyl dicarbonate

: 799561-34-5
(3aS,8aS)-3a-benzyl-1-methyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole

: 799561-68-5
3a-benzyl-1-methyl-2,3,3a,8a-tetrahydro-1H-pyrrolo[2,3-b]indole-8-carboxylic acid tert-butyl ester

Guidance literature:: (3aS,8aS)-3a-benzyl-1-methyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole; With sodium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 0.25h;

di-tert-butyl dicarbonate; In tetrahydrofuran; at -78 - 20 ℃;
DOI:10.1021/ja046690e

Reference yield:

: 799561-33-4
(S)-(1,3-dibenzyl-2-oxo-2,3-dihydro-1H-indol-3-yl)acetaldehyde

: 799561-68-5
3a-benzyl-1-methyl-2,3,3a,8a-tetrahydro-1H-pyrrolo[2,3-b]indole-8-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: Et₃N; MgSO₄ / tetrahydrofuran / 48 h / 20 °C

1.2: 58 percent / LiAlH₄ / tetrahydrofuran / 1.5 h / Heating

2.1: 86 percent / Na; NH₃ / tetrahydrofuran / 0.25 h / -78 °C

3.1: NaHMDS / tetrahydrofuran / 0.25 h / -78 °C

3.2: 79 percent / tetrahydrofuran / -78 - 20 °C

With ammonia; sodium hexamethyldisilazane; sodium; magnesium sulfate; triethylamine; In tetrahydrofuran;
DOI:10.1021/ja046690e

Reference yield:

: 799561-41-4
(3aS,8aR)-3a,8-dibenzyl-1-methyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole

: 799561-68-5
3a-benzyl-1-methyl-2,3,3a,8a-tetrahydro-1H-pyrrolo[2,3-b]indole-8-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 2 steps

1.1: 86 percent / Na; NH₃ / tetrahydrofuran / 0.25 h / -78 °C

2.1: NaHMDS / tetrahydrofuran / 0.25 h / -78 °C

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

With ammonia; sodium hexamethyldisilazane; sodium; In tetrahydrofuran;
DOI:10.1021/ja046690e