(1R,4S,5S,6R)-6-[(4-methoxyphenyl)methoxy]-1,3,3-trimethyl-2-methylene-5-(phenylmethoxy)bicyclo[2.2.2]octane

Base Information

Chemical Name:(1R,4S,5S,6R)-6-[(4-methoxyphenyl)methoxy]-1,3,3-trimethyl-2-methylene-5-(phenylmethoxy)bicyclo[2.2.2]octane
CAS No.:210633-76-4
Molecular Formula:C₂₇H₃₄O₃
Molecular Weight:406.565
Hs Code.:

Synonyms:(1R,4S,5S,6R)-6-[(4-methoxyphenyl)methoxy]-1,3,3-trimethyl-2-methylene-5-(phenylmethoxy)bicyclo[2.2.2]octane

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Chemical Property of (1R,4S,5S,6R)-6-[(4-methoxyphenyl)methoxy]-1,3,3-trimethyl-2-methylene-5-(phenylmethoxy)bicyclo[2.2.2]octane

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Technology Process of (1R,4S,5S,6R)-6-[(4-methoxyphenyl)methoxy]-1,3,3-trimethyl-2-methylene-5-(phenylmethoxy)bicyclo[2.2.2]octane

There total 3 articles about (1R,4S,5S,6R)-6-[(4-methoxyphenyl)methoxy]-1,3,3-trimethyl-2-methylene-5-(phenylmethoxy)bicyclo[2.2.2]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: 92.0%

: 100-39-0
benzyl bromide

: 210633-74-2
(1S,2S,3R,4R)-3-[(4-methoxyphenyl)methoxy]-4,6,6-trimethyl-5-methylenebicyclo[2.2.2]octan-2-ol

: 210633-76-4
(1R,4S,5S,6R)-6-[(4-methoxyphenyl)methoxy]-1,3,3-trimethyl-2-methylene-5-(phenylmethoxy)bicyclo[2.2.2]octane

Guidance literature:: With tetra-(n-butyl)ammonium iodide; sodium hydride; In N,N-dimethyl-formamide; at 18 ℃; for 15h;
DOI:10.1055/s-1998-1801

Reference yield:

: 210633-71-9
(2S,3aR,4S,7S,7aS)-tetrahydro-2-(4-methoxyphenyl)-4,6,6-trimethyl-4,7-ethano-1,3-benzodioxol-5(4H)-one

: 210633-76-4
(1R,4S,5S,6R)-6-[(4-methoxyphenyl)methoxy]-1,3,3-trimethyl-2-methylene-5-(phenylmethoxy)bicyclo[2.2.2]octane

Guidance literature:: Multi-step reaction with 3 steps

1.1: n-butyllithium / tetrahydrofuran / 2 h / -10 - 18 °C

1.2: 99 percent / tetrahydrofuran / 0.5 h

2.1: 83 percent / diisobutylaluminium hydride / CH₂Cl₂; pentane; hexane / 5.5 h / -60 - -40 °C

3.1: 92 percent / sodium hydride; tetrabutylammonium iodide / dimethylformamide / 5 h / 18 °C

With n-butyllithium; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; pentane;
DOI:10.1071/CH03161

Reference yield:

: 210633-72-0
(2S,3aR,4R,7S,7aS)-hexahydro-2-(4-methoxyphenyl)-4,6,6-trimethyl-5-methylene-4,7-ethano-1,3-benzodioxole

: 210633-76-4
(1R,4S,5S,6R)-6-[(4-methoxyphenyl)methoxy]-1,3,3-trimethyl-2-methylene-5-(phenylmethoxy)bicyclo[2.2.2]octane

Guidance literature:: Multi-step reaction with 2 steps

1: 83 percent / diisobutylaluminium hydride / CH₂Cl₂; pentane; hexane / 5.5 h / -60 - -40 °C

2: 92 percent / sodium hydride; tetrabutylammonium iodide / dimethylformamide / 5 h / 18 °C

With tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; In hexane; dichloromethane; N,N-dimethyl-formamide; pentane;
DOI:10.1071/CH03161