(S)-tert-butyl 1-o-tolyl-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate

Base Information

Chemical Name:(S)-tert-butyl 1-o-tolyl-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate
CAS No.:1335207-79-8
Molecular Formula:C₂₃H₂₆N₂O₂
Molecular Weight:362.472
Hs Code.:

Synonyms:(S)-tert-butyl 1-o-tolyl-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate

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Chemical Property of (S)-tert-butyl 1-o-tolyl-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate

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Technology Process of (S)-tert-butyl 1-o-tolyl-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate

There total 8 articles about (S)-tert-butyl 1-o-tolyl-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-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: 80.0%

: 21109-25-1
1-(1H-indol-2-yl)methanamine

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

: 529-20-4
2-methylphenyl aldehyde

: 1335207-79-8
(S)-tert-butyl 1-o-tolyl-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate

Guidance literature:: 1-(1H-indol-2-yl)methanamine; 2-methylphenyl aldehyde; With (S)-N-benzhydryl-2-{{2-{[3,5-bis(trifluoromethyl)phenyl]amino}-3,4-dioxocyclobut-1-en-1-yl}amino}-N,3,3-trimethylbutanamide; benzoic acid; In toluene; at 22 ℃; for 1h; Molecular sieve; Inert atmosphere;

di-tert-butyl dicarbonate; In toluene; at 22 ℃; for 0.5h; Molecular sieve; Inert atmosphere;

In hexane; enantioselective reaction;
DOI:10.1002/adsc.202001472

Reference yield: 77.0%

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

: 1-o-tolyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole

: 1335207-79-8
(S)-tert-butyl 1-o-tolyl-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate

: (R)-tert-butyl 1-o-tolyl-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate

Guidance literature:: In toluene; for 0.5h; Inert atmosphere;
DOI:10.1021/ol202300t

Reference yield:

: 120-72-9
indole

: 1335207-79-8
(S)-tert-butyl 1-o-tolyl-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate

: (R)-tert-butyl 1-o-tolyl-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate

Guidance literature:: Multi-step reaction with 7 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere

1.2: -78 - 4 °C

2.1: pyridine / dichloromethane / 2 h / 4 °C

3.1: sodium azide / N,N-dimethyl-formamide / 60 °C

4.1: triphenylphosphine / tetrahydrofuran / 4 h / 22 °C

5.1: water / tetrahydrofuran

6.1: (S)-N-benzhydryl-2-(3-(3,5-bis(trifluoromethyl)phenyl)thioureido)-N,3,3-trimethyl butanamide; benzoic acid / toluene / 2 h / 22 °C / Inert atmosphere

7.1: toluene / 0.5 h / Inert atmosphere

With pyridine; n-butyllithium; sodium azide; (S)-N-benzhydryl-2-(3-(3,5-bis(trifluoromethyl)phenyl)thioureido)-N,3,3-trimethyl butanamide; water; triphenylphosphine; benzoic acid; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; 6.1: iso-Pictet-Spengler reaction;
DOI:10.1021/ol202300t