3a-benzyl-7-iodo-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-7-iodo-1-methyl-2,3,3a,8a-tetrahydro-1H-pyrrolo[2,3-b]indole-8-carboxylic acid tert-butyl ester
CAS No.:799561-69-6
Molecular Formula:C₂₃H₂₇IN₂O₂
Molecular Weight:490.384
Hs Code.:

3a-benzyl-7-iodo-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-7-iodo-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-7-iodo-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-7-iodo-1-methyl-2,3,3a,8a-tetrahydro-1H-pyrrolo[2,3-b]indole-8-carboxylic acid tert-butyl ester

There total 5 articles about 3a-benzyl-7-iodo-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: 89.0%

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

: 799561-69-6
3a-benzyl-7-iodo-1-methyl-2,3,3a,8a-tetrahydro-1H-pyrrolo[2,3-b]indole-8-carboxylic acid tert-butyl ester

Guidance literature:: 3a-benzyl-1-methyl-2,3,3a,8a-tetrahydro-1H-pyrrolo[2,3-b]indole-8-carboxylic acid tert-butyl ester; With N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium; In diethyl ether; cyclohexane; at -78 ℃; for 0.5h;

With diodoethane; In diethyl ether; cyclohexane; at 0 ℃; for 0.5h;
DOI:10.1021/ja046690e

Reference yield:

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

: 799561-69-6
3a-benzyl-7-iodo-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: NaHMDS / tetrahydrofuran / 0.25 h / -78 °C

1.2: 79 percent / tetrahydrofuran / -78 - 20 °C

2.1: sec-BuLi; TMEDA / cyclohexane; diethyl ether / 0.5 h / -78 °C

2.2: 89 percent / diodoethane / cyclohexane; diethyl ether / 0.5 h / 0 °C

With N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium; sodium hexamethyldisilazane; In tetrahydrofuran; diethyl ether; cyclohexane;
DOI:10.1021/ja046690e

Reference yield:

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

: 799561-69-6
3a-benzyl-7-iodo-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 4 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

4.1: sec-BuLi; TMEDA / cyclohexane; diethyl ether / 0.5 h / -78 °C

4.2: 89 percent / diodoethane / cyclohexane; diethyl ether / 0.5 h / 0 °C

With N,N,N,N,-tetramethylethylenediamine; ammonia; sec.-butyllithium; sodium hexamethyldisilazane; sodium; magnesium sulfate; triethylamine; In tetrahydrofuran; diethyl ether; cyclohexane;
DOI:10.1021/ja046690e