Technology Process of (5aS,8aR)-5-(3,4,5-trimethoxyphenyl)-5,8,8a,9-tetrahydro-1,3-dioxolo[4,5-g]furo[3,4-b]quinolin-6(5aH)-one
There total 11 articles about (5aS,8aR)-5-(3,4,5-trimethoxyphenyl)-5,8,8a,9-tetrahydro-1,3-dioxolo[4,5-g]furo[3,4-b]quinolin-6(5aH)-one which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
With
dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate;
In
toluene;
at 80 ℃;
for 24h;
Reagent/catalyst;
Inert atmosphere;
Schlenk technique;
DOI:10.1055/s-0033-1338414
- Guidance literature:
-
Multi-step reaction with 3 steps
1.1: D-Prolin / tetrahydrofuran / 16 h / 4 °C
2.1: sodium tetrahydroborate / tetrahydrofuran / 0.5 h / 0 °C
2.2: 1 h
3.1: caesium carbonate; tris-(dibenzylideneacetone)dipalladium(0); dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane / toluene / 24 h / 80 °C / Inert atmosphere; Schlenk technique
With
dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; sodium tetrahydroborate; tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; D-Prolin;
In
tetrahydrofuran; toluene;
1.1: |Mannich Aminomethylation / 3.1: |Buchwald-Hartwig Coupling;
DOI:10.1055/s-0033-1338414
- Guidance literature:
-
Multi-step reaction with 8 steps
1.1: sulfuric acid / 24 h / Reflux
2.1: hydrogen; palladium 10% on activated carbon / methanol / 20 °C / 2844.39 Torr / Autoclave
3.1: bromine / dichloromethane / 0 °C
4.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 °C / Inert atmosphere
5.1: dimethyl sulfoxide; oxalyl dichloride / dichloromethane / 4 h / -78 °C
5.2: 0.25 h / -78 °C
6.1: D-Prolin / tetrahydrofuran / 16 h / 4 °C
7.1: sodium tetrahydroborate / tetrahydrofuran / 0.5 h / 0 °C
7.2: 1 h
8.1: caesium carbonate; tris-(dibenzylideneacetone)dipalladium(0); dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane / toluene / 24 h / 80 °C / Inert atmosphere; Schlenk technique
With
dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; sodium tetrahydroborate; tris-(dibenzylideneacetone)dipalladium(0); lithium aluminium tetrahydride; oxalyl dichloride; sulfuric acid; palladium 10% on activated carbon; hydrogen; bromine; caesium carbonate; dimethyl sulfoxide; D-Prolin;
In
tetrahydrofuran; methanol; dichloromethane; toluene;
5.1: |Swern Oxidation / 5.2: |Swern Oxidation / 6.1: |Mannich Aminomethylation / 8.1: |Buchwald-Hartwig Coupling;
DOI:10.1055/s-0033-1338414
![(3R,4R)-4-[(6-bromo-1,3-benzodioxol-5-yl)methyl]-3-[(3,4,5-trimethoxyphenyl)amino]dihydrofuran-2(3H)-one](/Databaselist/images/loading.webp)
