dimethyl 3-[3-[N-(S)-α-methylbenzyl-N-tert-butoxycarbonylamino]propyl]indole-2-propanedioate

Base Information

Chemical Name:dimethyl 3-[3-[N-(S)-α-methylbenzyl-N-tert-butoxycarbonylamino]propyl]indole-2-propanedioate
CAS No.:360787-65-1
Molecular Formula:C₂₉H₃₆N₂O₆
Molecular Weight:508.615
Hs Code.:

Synonyms:dimethyl 3-[3-[N-(S)-α-methylbenzyl-N-tert-butoxycarbonylamino]propyl]indole-2-propanedioate

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Chemical Property of dimethyl 3-[3-[N-(S)-α-methylbenzyl-N-tert-butoxycarbonylamino]propyl]indole-2-propanedioate

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Technology Process of dimethyl 3-[3-[N-(S)-α-methylbenzyl-N-tert-butoxycarbonylamino]propyl]indole-2-propanedioate

There total 10 articles about dimethyl 3-[3-[N-(S)-α-methylbenzyl-N-tert-butoxycarbonylamino]propyl]indole-2-propanedioate 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: 87.0%

: 360787-64-0
[3-(1H-indol-3-yl)-propyl]-(1-phenyl-ethyl)-carbamic acid tert-butyl ester

: thallium dimethylmalonate

: 360787-65-1
dimethyl 3-[3-[N-(S)-α-methylbenzyl-N-tert-butoxycarbonylamino]propyl]indole-2-propanedioate

Guidance literature:: [3-(1H-indol-3-yl)-propyl]-(1-phenyl-ethyl)-carbamic acid tert-butyl ester; With tert-butylhypochlorite; triethylamine; In tetrahydrofuran; at -78 ℃; for 0.25h;

thallium dimethylmalonate; In tetrahydrofuran; at 20 ℃; for 2h; Further stages.;
DOI:10.1021/jo000249z

Reference yield:

: [3-(3-chloro-3H-indol-3-yl)-propyl]-(1-phenyl-ethyl)-carbamic acid tert-butyl ester

: lithium dimethylmalonate

: 360787-65-1
dimethyl 3-[3-[N-(S)-α-methylbenzyl-N-tert-butoxycarbonylamino]propyl]indole-2-propanedioate

Guidance literature:: With zinc(II) chloride; In tetrahydrofuran; diethyl ether; at 20 ℃; for 6h;
DOI:10.1021/jo000249z

Reference yield:

: 120-72-9
indole

: 360787-65-1
dimethyl 3-[3-[N-(S)-α-methylbenzyl-N-tert-butoxycarbonylamino]propyl]indole-2-propanedioate

Guidance literature:: Multi-step reaction with 6 steps

1.1: 49 percent / copper (II) acetate; acetic acid; boric acid / benzene / 8 h / 180 °C

2.1: 73 percent / DIBALH / CH₂Cl₂ / -60 - 25 °C

3.1: benzene / 0.33 h / Heating

3.2: 2.3 g / sodium borohydride / methanol / 0.5 h / 0 °C

4.1: 96 percent / NaOH / tetrahydrofuran / 0 - 25 °C

5.1: triethylamine; t-butyl hypochlorite / tetrahydrofuran / 0.33 h / -60 °C

6.1: 2.89 g / zinc chloride / tetrahydrofuran; diethyl ether / 6 h / 20 °C

With sodium hydroxide; tert-butylhypochlorite; copper diacetate; boric acid; diisobutylaluminium hydride; acetic acid; triethylamine; zinc(II) chloride; In tetrahydrofuran; diethyl ether; dichloromethane; benzene;
DOI:10.1021/jo000249z