methyl 2-(2-bromoethyloxybenzyl)-4-(cis-3a,4,5,6,7,7a-hexahydroisoindolin-2-yl)-4-oxobutanoate

Base Information

Chemical Name:methyl 2-(2-bromoethyloxybenzyl)-4-(cis-3a,4,5,6,7,7a-hexahydroisoindolin-2-yl)-4-oxobutanoate
CAS No.:1613033-36-5
Molecular Formula:C₂₂H₃₀BrNO₄
Molecular Weight:452.388
Hs Code.:

Synonyms:methyl 2-(2-bromoethyloxybenzyl)-4-(cis-3a,4,5,6,7,7a-hexahydroisoindolin-2-yl)-4-oxobutanoate

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Chemical Property of methyl 2-(2-bromoethyloxybenzyl)-4-(cis-3a,4,5,6,7,7a-hexahydroisoindolin-2-yl)-4-oxobutanoate

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Technology Process of methyl 2-(2-bromoethyloxybenzyl)-4-(cis-3a,4,5,6,7,7a-hexahydroisoindolin-2-yl)-4-oxobutanoate

There total 7 articles about methyl 2-(2-bromoethyloxybenzyl)-4-(cis-3a,4,5,6,7,7a-hexahydroisoindolin-2-yl)-4-oxobutanoate 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: 60.0%

: 1613033-24-1
methyl 2-(2-hydroxybenzyl)-4-(cis-3a,4,5,6,7,7a-hexahydroisoindolin-2-yl)-4-oxobutanoate

: 19263-21-9
2-bromoethyl p-toluenesulfonate

: 1613033-36-5
methyl 2-(2-bromoethyloxybenzyl)-4-(cis-3a,4,5,6,7,7a-hexahydroisoindolin-2-yl)-4-oxobutanoate

Guidance literature:: With caesium carbonate; In N,N-dimethyl-formamide; at 40 ℃;
DOI:10.1016/j.bmc.2014.04.059

Reference yield:

: 5896-17-3
2-(phenylmethoxy)benzaldehyde

: 1613033-36-5
methyl 2-(2-bromoethyloxybenzyl)-4-(cis-3a,4,5,6,7,7a-hexahydroisoindolin-2-yl)-4-oxobutanoate

Guidance literature:: Multi-step reaction with 7 steps

1: potassium hydroxide / dimethyl sulfoxide / 15 h / 80 °C

2: sodium hydroxide; water / dimethyl sulfoxide / 5 h / 120 °C

3: acetic anhydride / dichloromethane / 1.5 h / 60 °C

4: dichloromethane / 5 h / 0 - 20 °C

5: thionyl chloride / 15.5 h / 0 - 20 °C

6: palladium 10% on activated carbon; hydrogen / methanol / 760.05 Torr

7: caesium carbonate / N,N-dimethyl-formamide / 40 °C

With thionyl chloride; palladium 10% on activated carbon; water; hydrogen; acetic anhydride; caesium carbonate; potassium hydroxide; sodium hydroxide; In methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1016/j.bmc.2014.04.059

Reference yield:

: 1613033-20-7
2-(2-benzyloxybenzylidene)succinic acid

: 1613033-36-5
methyl 2-(2-bromoethyloxybenzyl)-4-(cis-3a,4,5,6,7,7a-hexahydroisoindolin-2-yl)-4-oxobutanoate

Guidance literature:: Multi-step reaction with 5 steps

1: acetic anhydride / dichloromethane / 1.5 h / 60 °C

2: dichloromethane / 5 h / 0 - 20 °C

3: thionyl chloride / 15.5 h / 0 - 20 °C

4: palladium 10% on activated carbon; hydrogen / methanol / 760.05 Torr

5: caesium carbonate / N,N-dimethyl-formamide / 40 °C

With thionyl chloride; palladium 10% on activated carbon; hydrogen; acetic anhydride; caesium carbonate; In methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/j.bmc.2014.04.059