(1R,2R,4S,E)-7-tert-butyl 2-cyclohexyl 3-(2-ethylbutylidene)-7-azabicyclo[2.2.1]hept-5-ene-2,7-dicarboxylate

Base Information

Chemical Name:(1R,2R,4S,E)-7-tert-butyl 2-cyclohexyl 3-(2-ethylbutylidene)-7-azabicyclo[2.2.1]hept-5-ene-2,7-dicarboxylate
CAS No.:1427662-74-5
Molecular Formula:C₂₄H₃₇NO₄
Molecular Weight:403.562
Hs Code.:

Synonyms:(1R,2R,4S,E)-7-tert-butyl 2-cyclohexyl 3-(2-ethylbutylidene)-7-azabicyclo[2.2.1]hept-5-ene-2,7-dicarboxylate

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Chemical Property of (1R,2R,4S,E)-7-tert-butyl 2-cyclohexyl 3-(2-ethylbutylidene)-7-azabicyclo[2.2.1]hept-5-ene-2,7-dicarboxylate

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Technology Process of (1R,2R,4S,E)-7-tert-butyl 2-cyclohexyl 3-(2-ethylbutylidene)-7-azabicyclo[2.2.1]hept-5-ene-2,7-dicarboxylate

There total 3 articles about (1R,2R,4S,E)-7-tert-butyl 2-cyclohexyl 3-(2-ethylbutylidene)-7-azabicyclo[2.2.1]hept-5-ene-2,7-dicarboxylate 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: 57.0%

: 5176-27-2
N-tert-butyloxycarbonyl-pyrrole

: (S)-(+)-cyclohexyl 5-ethylhepta-2,3-dienoate

: 1427662-74-5
(1R,2R,4S,E)-7-tert-butyl 2-cyclohexyl 3-(2-ethylbutylidene)-7-azabicyclo[2.2.1]hept-5-ene-2,7-dicarboxylate

Guidance literature:: (S)-(+)-cyclohexyl 5-ethylhepta-2,3-dienoate; With aluminum (III) chloride; In dichloromethane; at -78 ℃; for 0.5h; Inert atmosphere;

N-tert-butyloxycarbonyl-pyrrole; In dichloromethane; at -78 ℃; for 48h; Inert atmosphere;
DOI:10.1021/ja401606e

Reference yield:

: 1427662-73-4
(E)-cyclohexyl 5-ethyl-3-(((trifluoromethyl)sulfonyl)oxy)hept-2-enoate

: 1427662-74-5
(1R,2R,4S,E)-7-tert-butyl 2-cyclohexyl 3-(2-ethylbutylidene)-7-azabicyclo[2.2.1]hept-5-ene-2,7-dicarboxylate

Guidance literature:: Multi-step reaction with 2 steps

1.1: N-ethyl-N,N-diisopropylamine; C₅₉H₄₉O₃P; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ / Isopropyl acetate / 9 h / 20 °C / Inert atmosphere

2.1: aluminum (III) chloride / dichloromethane / 0.5 h / -78 °C / Inert atmosphere

2.2: 48 h / -78 °C / Inert atmosphere

With aluminum (III) chloride; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; C₅₉H₄₉O₃P; N-ethyl-N,N-diisopropylamine; In dichloromethane; Isopropyl acetate; 2.1: |Diels-Alder Cycloaddition;
DOI:10.1021/ja401606e

Reference yield:

: 1427663-02-2
C₁₅H₂₆O₃

: 1427662-74-5
(1R,2R,4S,E)-7-tert-butyl 2-cyclohexyl 3-(2-ethylbutylidene)-7-azabicyclo[2.2.1]hept-5-ene-2,7-dicarboxylate

Guidance literature:: Multi-step reaction with 3 steps

1.1: tetramethyl ammoniumhydroxide / hexane; water / 5 - 15 °C / Inert atmosphere

2.1: N-ethyl-N,N-diisopropylamine; C₅₉H₄₉O₃P; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ / Isopropyl acetate / 9 h / 20 °C / Inert atmosphere

3.1: aluminum (III) chloride / dichloromethane / 0.5 h / -78 °C / Inert atmosphere

3.2: 48 h / -78 °C / Inert atmosphere

With aluminum (III) chloride; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; C₅₉H₄₉O₃P; tetramethyl ammoniumhydroxide; N-ethyl-N,N-diisopropylamine; In hexane; dichloromethane; Isopropyl acetate; water; 3.1: |Diels-Alder Cycloaddition;
DOI:10.1021/ja401606e