phenylmethyl 4-({1-[(tert-butyl)oxycarbonyl]indol-2-yl}ethylidene)-3-ethylidenepiperidine-1-carboxylate

Base Information

Chemical Name:phenylmethyl 4-({1-[(tert-butyl)oxycarbonyl]indol-2-yl}ethylidene)-3-ethylidenepiperidine-1-carboxylate
CAS No.:261895-13-0
Molecular Formula:C₃₀H₃₄N₂O₄
Molecular Weight:486.611
Hs Code.:

Synonyms:phenylmethyl 4-({1-[(tert-butyl)oxycarbonyl]indol-2-yl}ethylidene)-3-ethylidenepiperidine-1-carboxylate

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Chemical Property of phenylmethyl 4-({1-[(tert-butyl)oxycarbonyl]indol-2-yl}ethylidene)-3-ethylidenepiperidine-1-carboxylate

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Technology Process of phenylmethyl 4-({1-[(tert-butyl)oxycarbonyl]indol-2-yl}ethylidene)-3-ethylidenepiperidine-1-carboxylate

There total 5 articles about phenylmethyl 4-({1-[(tert-butyl)oxycarbonyl]indol-2-yl}ethylidene)-3-ethylidenepiperidine-1-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: 64.0%

: lithium triethyl(1-tert-butoxycarbonylindol-2-yl)borate

: 260430-49-7
N-(2-bromobut-2-enyl)-N-pent-3-ynyl(phenylmethoxy)carboxamide

: 261895-13-0
phenylmethyl 4-({1-[(tert-butyl)oxycarbonyl]indol-2-yl}ethylidene)-3-ethylidenepiperidine-1-carboxylate

Guidance literature:: With triphenylphosphine; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; In tetrahydrofuran; at 60 ℃;
DOI:10.3987/COM-99-8759

Reference yield: 64.0%

: 75400-67-8
indole-1-carboxylic acid tert-butyl ester

: 260430-49-7
N-(2-bromobut-2-enyl)-N-pent-3-ynyl(phenylmethoxy)carboxamide

: 261895-13-0
phenylmethyl 4-({1-[(tert-butyl)oxycarbonyl]indol-2-yl}ethylidene)-3-ethylidenepiperidine-1-carboxylate

Guidance literature:: indole-1-carboxylic acid tert-butyl ester; With tert.-butyl lithium; In tetrahydrofuran; at -78 ℃;

With triethyl borane; In tetrahydrofuran;

N-(2-bromobut-2-enyl)-N-pent-3-ynyl(phenylmethoxy)carboxamide; With Pd₂(PPh₃)2Cl₂; In tetrahydrofuran; at 60 ℃; for 4h;
DOI:10.1016/S0040-4020(99)01016-9

Reference yield:

: 54106-83-1
pent-3-ynyl triflate

: 261895-13-0
phenylmethyl 4-({1-[(tert-butyl)oxycarbonyl]indol-2-yl}ethylidene)-3-ethylidenepiperidine-1-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1.1: 9.9 g / diisopropylethylamine / CH₂Cl₂ / 20 °C

2.1: 78 percent / triethylamine / CH₂Cl₂ / 2 h / 20 °C

3.1: tert-butyllithium / tetrahydrofuran / -78 °C

3.2: triethylborane / tetrahydrofuran

3.3: 64 percent / Pd₂Cl₂(PPh₃)2 / tetrahydrofuran / 4 h / 60 °C

With tert.-butyl lithium; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; 1.1: Alkylation / 2.1: Acylation / 3.1: Metallation / 3.2: Substitution / 3.3: Cyclization;
DOI:10.1016/S0040-4020(99)01016-9