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

Base Information

• Chemical Name: endo-2-(hydroxymethyl)-exo-3,3-diphenyl-anti-8-tert-butoxytricyclo<3.2.1.0^2,4>octane
• CAS No.: 82521-79-7
• Molecular Formula: C₂₅H₃₀O₂
• Molecular Weight: 362.512

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

Chemical Property of endo-2-(hydroxymethyl)-exo-3,3-diphenyl-anti-8-tert-butoxytricyclo<3.2.1.0^2,4>octane

Chemical Property:

Purity/Quality:

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Technology Process of endo-2-(hydroxymethyl)-exo-3,3-diphenyl-anti-8-tert-butoxytricyclo<3.2.1.0^2,4>octane

There total 7 articles about endo-2-(hydroxymethyl)-exo-3,3-diphenyl-anti-8-tert-butoxytricyclo<3.2.1.0^2,4>octane 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: 96.0%

endo-2-(carbomethoxy)-exo-3,3-diphenyl-anti-8-tert-butoxytricyclo<3.2.1.02,4>octane (82521-77-5) → endo-2-(hydroxymethyl)-exo-3,3-diphenyl-anti-8-tert-butoxytricyclo<3.2.1.02,4>octane (82521-79-7)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; at 25 ℃; for 10h;

DOI:10.1021/jo00140a026

Reference yield:

2-bromo-anti-7-tert-butoxynorbornene (82521-66-2) → endo-2-(hydroxymethyl)-exo-3,3-diphenyl-anti-8-tert-butoxytricyclo<3.2.1.02,4>octane (82521-79-7)

Guidance literature:

Multi-step reaction with 6 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

5: 86 percent / toluene / Heating

6: 96 percent / lithium aluminum hydride / diethyl ether / 10 h / 25 °C

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

DOI:10.1021/jo00140a026

Reference yield:

2-cyano-anti-7-tert-butoxynorbornene (82521-67-3) → endo-2-(hydroxymethyl)-exo-3,3-diphenyl-anti-8-tert-butoxytricyclo<3.2.1.02,4>octane (82521-79-7)

Guidance literature:

Multi-step reaction with 5 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

4: 86 percent / toluene / Heating

5: 96 percent / lithium aluminum hydride / diethyl ether / 10 h / 25 °C

With potassium hydroxide; sodium hydroxide; lithium aluminium tetrahydride; hydroquinone; In diethyl ether; water; toluene; Petroleum ether;

DOI:10.1021/jo00140a026

upstream raw materials:

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

2-bromo-anti-7-tert-butoxynorbornene

2-cyano-anti-7-tert-butoxynorbornene

anti-7-tert-butoxynorbornene-2-carboxylic acid

Downstream raw materials:

endo-2-formyl-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-vinyl-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 acetate

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