endo-2-(carbomethoxy)-exo-(3,4-diaza-5,5-diphenyl)-anti-10-tert-butoxytricyclo<5.2.1.0^2,6>dec-3-ene

Base Information

• Chemical Name: endo-2-(carbomethoxy)-exo-(3,4-diaza-5,5-diphenyl)-anti-10-tert-butoxytricyclo<5.2.1.0^2,6>dec-3-ene
• CAS No.: 82521-71-9
• Molecular Formula: C₂₆H₃₀N₂O₃
• Molecular Weight: 418.536

Synonyms:endo-2-(carbomethoxy)-exo-(3,4-diaza-5,5-diphenyl)-anti-10-tert-butoxytricyclo<5.2.1.0^2,6>dec-3-ene

Chemical Property of endo-2-(carbomethoxy)-exo-(3,4-diaza-5,5-diphenyl)-anti-10-tert-butoxytricyclo<5.2.1.0^2,6>dec-3-ene

Chemical Property:

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Technology Process of endo-2-(carbomethoxy)-exo-(3,4-diaza-5,5-diphenyl)-anti-10-tert-butoxytricyclo<5.2.1.0^2,6>dec-3-ene

There total 5 articles about endo-2-(carbomethoxy)-exo-(3,4-diaza-5,5-diphenyl)-anti-10-tert-butoxytricyclo<5.2.1.0^2,6>dec-3-ene 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: 10.0%

methyl anti-7-tert-butoxynorbornene-2-carboxylate (82521-69-5) + diazodiphenylmethane (908093-98-1) → endo-2-(carbomethoxy)-exo-(3,4-diaza-5,5-diphenyl)-anti-10-tert-butoxytricyclo<5.2.1.02,6>dec-3-ene (82521-71-9) + endo-6-(carbomethoxy)-exo-(3,4-diaza-5,5-diphenyl)-anti-10-tert-butoxytricyclo<5.2.1.02,6>dec-3-ene (82521-73-1)

Guidance literature:

With hydroquinone; In diethyl ether; Petroleum ether; Ambient temperature; 2-3 weeks;

DOI:10.1021/jo00140a026

Reference yield:

2-bromo-anti-7-tert-butoxynorbornene (82521-66-2) → endo-2-(carbomethoxy)-exo-(3,4-diaza-5,5-diphenyl)-anti-10-tert-butoxytricyclo<5.2.1.02,6>dec-3-ene (82521-71-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 86 percent / copper(I) cyanide / dimethylformamide / 11 h / Heating

2: 45 percent / potassium hydroxide / H₂O / 24 h / Heating

3: 1.) 25percent aq. sodium hydroxide / 1.) HMPA, 25 deg C, 2 h, 2.) HMPA, 25 deg C, 6 h

4: 70 percent / hydroquinone / petroleum ether; diethyl ether / Ambient temperature; 2-3 weeks

With potassium hydroxide; sodium hydroxide; copper(l) cyanide; hydroquinone; In diethyl ether; water; N,N-dimethyl-formamide; Petroleum ether;

DOI:10.1021/jo00140a026

Reference yield:

2-cyano-anti-7-tert-butoxynorbornene (82521-67-3) → endo-2-(carbomethoxy)-exo-(3,4-diaza-5,5-diphenyl)-anti-10-tert-butoxytricyclo<5.2.1.02,6>dec-3-ene (82521-71-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 45 percent / potassium hydroxide / H₂O / 24 h / Heating

2: 1.) 25percent aq. sodium hydroxide / 1.) HMPA, 25 deg C, 2 h, 2.) HMPA, 25 deg C, 6 h

3: 70 percent / hydroquinone / petroleum ether; diethyl ether / Ambient temperature; 2-3 weeks

With potassium hydroxide; sodium hydroxide; hydroquinone; In diethyl ether; water; Petroleum ether;

DOI:10.1021/jo00140a026

upstream raw materials:

methyl anti-7-tert-butoxynorbornene-2-carboxylate

diazodiphenylmethane

2-bromo-anti-7-tert-butoxynorbornene

2-cyano-anti-7-tert-butoxynorbornene

Downstream raw materials:

endo-2-(carbomethoxy)-exo-3,3-diphenyl-anti-8-tert-butoxytricyclo<3.2.1.0^2,4>octane

endo-2-ethyl-exo-3,3-diphenyltricyclo<3.2.1.0^2,4>oct-anti-8-yl tosylate

endo-2-formyl-exo-3,3-diphenyl-anti-8-tert-butoxytricyclo<3.2.1.0^2,4>octane

endo-2-vinyl-exo-3,3-diphenyl-anti-8-tert-butoxytricyclo<3.2.1.0^2,4>octane

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