(8aα,10β,11α,12β,12aα,13aα)-(+/-)-5,8,8a,9,10,11,12,12a,13,13a-decahydro-2,3,11-trimethoxy-10-(3,4,5-trimethoxybenzoyloxy)-6H-dibenzoquinolizine-12-carbonitrile

Base Information

Chemical Name:(8aα,10β,11α,12β,12aα,13aα)-(+/-)-5,8,8a,9,10,11,12,12a,13,13a-decahydro-2,3,11-trimethoxy-10-(3,4,5-trimethoxybenzoyloxy)-6H-dibenzoquinolizine-12-carbonitrile
CAS No.:113557-47-4
Molecular Formula:C₃₁H₃₈N₂O₈
Molecular Weight:566.651
Hs Code.:

(8aα,10β,11α,12β,12aα,13aα)-(+/-)-5,8,8a,9,10,11,12,12a,13,13a-decahydro-2,3,11-trimethoxy-10-(3,4,5-trimethoxybenzoyloxy)-6H-dibenzo<a,g>quinolizine-12-carbonitrile

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Chemical Property of (8aα,10β,11α,12β,12aα,13aα)-(+/-)-5,8,8a,9,10,11,12,12a,13,13a-decahydro-2,3,11-trimethoxy-10-(3,4,5-trimethoxybenzoyloxy)-6H-dibenzoquinolizine-12-carbonitrile

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Technology Process of (8aα,10β,11α,12β,12aα,13aα)-(+/-)-5,8,8a,9,10,11,12,12a,13,13a-decahydro-2,3,11-trimethoxy-10-(3,4,5-trimethoxybenzoyloxy)-6H-dibenzoquinolizine-12-carbonitrile

There total 24 articles about (8aα,10β,11α,12β,12aα,13aα)-(+/-)-5,8,8a,9,10,11,12,12a,13,13a-decahydro-2,3,11-trimethoxy-10-(3,4,5-trimethoxybenzoyloxy)-6H-dibenzoquinolizine-12-carbonitrile 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: 37.0%

: 4521-61-3
3,4,5-Trimethoxybenzoyl chloride

: 113575-55-6
(8aα,11α,12β,12aα,13aα)-(+/-)-5,8,8a,9,10,11,12,12a,13,13a-decahydro-2,3,11-trimethoxy-10-oxo-6H-dibenzoquinolizine-12-carbonitrile

: 113557-47-4,113626-01-0
(8aα,10α,11α,12β,12aα,13aα)-(+/-)-5,8,8a,9,10,11,12,12a,13,13a-decahydro-2,3,11-trimethoxy-10-(3,4,5-trimethoxybenzoyloxy)-6H-dibenzoquinolizine-12-carbonitrile

: 113557-47-4,113626-01-0
(8aα,10β,11α,12β,12aα,13aα)-(+/-)-5,8,8a,9,10,11,12,12a,13,13a-decahydro-2,3,11-trimethoxy-10-(3,4,5-trimethoxybenzoyloxy)-6H-dibenzoquinolizine-12-carbonitrile

Guidance literature:: With dmap; triethylamine; In dichloromethane; for 20h; Ambient temperature;
DOI:10.3987/COM-92-6089

Reference yield: 37.0%

: 4521-61-3
3,4,5-Trimethoxybenzoyl chloride

: 113575-55-6
(8aα,11α,12β,12aα,13aα)-(+/-)-5,8,8a,9,10,11,12,12a,13,13a-decahydro-2,3,11-trimethoxy-10-oxo-6H-dibenzoquinolizine-12-carbonitrile

: 113557-47-4,113626-01-0
(8aα,10α,11α,12β,12aα,13aα)-(+/-)-5,8,8a,9,10,11,12,12a,13,13a-decahydro-2,3,11-trimethoxy-10-(3,4,5-trimethoxybenzoyloxy)-6H-dibenzoquinolizine-12-carbonitrile

: 113557-47-4,113626-01-0
(8aα,10β,11α,12β,12aα,13aα)-(+/-)-5,8,8a,9,10,11,12,12a,13,13a-decahydro-2,3,11-trimethoxy-10-(3,4,5-trimethoxybenzoyloxy)-6H-dibenzoquinolizine-12-carbonitrile

Guidance literature:: With dmap; triethylamine; In dichloromethane; for 20h; Ambient temperature;
DOI:10.3987/COM-92-6089

Reference yield:

: 4721-98-6
6,7-dimethoxy-1-methyl-3,4-dihydroisoquinoline

: 113557-47-4,113626-01-0
(8aα,10α,11α,12β,12aα,13aα)-(+/-)-5,8,8a,9,10,11,12,12a,13,13a-decahydro-2,3,11-trimethoxy-10-(3,4,5-trimethoxybenzoyloxy)-6H-dibenzoquinolizine-12-carbonitrile

Guidance literature:: Multi-step reaction with 8 steps

1: 99 percent / Et₃N / benzene / 1 h / Ambient temperature

2: 1.) sodium borohydride, lithium aluminum hydride, 2.) 10percent aq. HCl / 1.) benzene, ether, RT, 30 min, 2.) THF

3: 68 percent / benzene; CH₂Cl₂ / 3.5 h / Heating

4: 93 percent / p-toluenesulfonic acid / benzene / 0.67 h / Heating

5: 6 percent / methanol / 2 h / 60 °C

6: 50 percent / NaH / tetrahydrofuran; diethyl ether / 1 h / Heating

7: 60 percent / 4M aq. HCl / 2.5 h / 100 °C

8: dimethylaminopyridine, triethylamine / CH₂Cl₂ / 20 h / Ambient temperature

With hydrogenchloride; dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; sodium hydride; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; benzene;
DOI:10.3987/COM-92-6089