tert-butyl 5-(2-bromobenzyl)-7,8-dihydro-[1,3]dioxolo[4,5-g]isoquinoline-6(5H)-carboxylate

Base Information

Chemical Name:tert-butyl 5-(2-bromobenzyl)-7,8-dihydro-[1,3]dioxolo[4,5-g]isoquinoline-6(5H)-carboxylate
CAS No.:934355-59-6
Molecular Formula:C₂₂H₂₄BrNO₄
Molecular Weight:446.341
Hs Code.:

Synonyms:tert-butyl 5-(2-bromobenzyl)-7,8-dihydro-[1,3]dioxolo[4,5-g]isoquinoline-6(5H)-carboxylate

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Chemical Property of tert-butyl 5-(2-bromobenzyl)-7,8-dihydro-[1,3]dioxolo[4,5-g]isoquinoline-6(5H)-carboxylate

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Technology Process of tert-butyl 5-(2-bromobenzyl)-7,8-dihydro-[1,3]dioxolo[4,5-g]isoquinoline-6(5H)-carboxylate

There total 8 articles about tert-butyl 5-(2-bromobenzyl)-7,8-dihydro-[1,3]dioxolo[4,5-g]isoquinoline-6(5H)-carboxylate 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: 70.0%

: 934355-48-3
5-(2-bromobenzyl)-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinoline

: 24424-99-5
di-tert-butyl dicarbonate

: 934355-59-6
tert-butyl 5-(2-bromobenzyl)-7,8-dihydro-[1,3]dioxolo[4,5-g]isoquinoline-6(5H)-carboxylate

Guidance literature:: With N-ethyl-N,N-diisopropylamine; dmap; In dichloromethane; at 23 ℃;
DOI:10.1002/ejoc.200600674

Reference yield: 49.0%

: 24424-99-5
di-tert-butyl dicarbonate

: 87201-31-8
1-(2'-bromobenzyl)-3,4-dihydro-6,7-methylenedioxyisoquinoline

: 934355-59-6
tert-butyl 5-(2-bromobenzyl)-7,8-dihydro-[1,3]dioxolo[4,5-g]isoquinoline-6(5H)-carboxylate

Guidance literature:: 1-(2'-bromobenzyl)-3,4-dihydro-6,7-methylenedioxyisoquinoline; With sodium tetrahydroborate; In methanol; at 0 - 20 ℃; for 3.5h;

di-tert-butyl dicarbonate; With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20 ℃; for 17h;
DOI:10.1016/j.tetlet.2020.152599

Reference yield:

: 18698-97-0
ortho-bromophenylacetic acid

: 934355-59-6
tert-butyl 5-(2-bromobenzyl)-7,8-dihydro-[1,3]dioxolo[4,5-g]isoquinoline-6(5H)-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

1: (COCl₂); dimethylformamide / CH₂Cl₂ / 25 °C

2: Et₃N / CH₂Cl₂ / 25 °C

3: POCl₃ / CH₂Cl₂ / 12 h / Heating

4: NaBH₄ / methanol / 3 h / 23 °C

5: 70 percent / iPr₂EtN / DMAP / CH₂Cl₂ / 23 °C

With phosgene; sodium tetrahydroborate; triethylamine; N-ethyl-N,N-diisopropylamine; N,N-dimethyl-formamide; trichlorophosphate; dmap; In methanol; dichloromethane; 3: Bischler-Napieralski cyclization;
DOI:10.1002/ejoc.200600674