Technology Process of (2R,3S,11bR)-2-hydroxy-3-isobutyl-9,10-dimethoxy-2,3,6,7-tetrahydro-1H-pyrido[2,1-α]isoquinolin-4(11bH)-one
There total 18 articles about (2R,3S,11bR)-2-hydroxy-3-isobutyl-9,10-dimethoxy-2,3,6,7-tetrahydro-1H-pyrido[2,1-α]isoquinolin-4(11bH)-one which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
(2S,3R)-3-((tert-butyldimethylsilyl)oxy)-N-(4,5-dimethoxy-2-vinylphenethyl)-2-isobutylpent-4-enamide;
With
Hoveyda-Grubbs catalyst second generation;
In
toluene;
at 135 ℃;
for 12h;
With
toluene-4-sulfonic acid;
In
benzene;
at 20 ℃;
for 24h;
DOI:10.1021/ol301612q
- Guidance literature:
-
Multi-step reaction with 7 steps
1.1: pivaloyl chloride; triethylamine / tetrahydrofuran / 1.17 h / -78 - 20 °C
1.2: -78 - 20 °C
2.1: titanium tetrachloride / dichloromethane / 0.25 h / -78 °C
2.2: 2 h / -78 °C
2.3: 2 h / -78 - 0 °C
3.1: n-butyllithium; trimethylaluminum / hexane; dichloromethane / 0.5 h / 0 °C
3.2: 0 - 20 °C
4.1: dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; methanol; water / 0 - 20 °C
5.1: 2,6-dimethylpyridine / dichloromethane / 48 h / 0 - 20 °C
5.2: 1.5 h / 20 °C
6.1: 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 0.33 h / 20 °C
6.2: 20 °C
7.1: Hoveyda-Grubbs catalyst second generation / toluene / 12 h / 135 °C
7.2: 24 h / 20 °C
With
2,6-dimethylpyridine; n-butyllithium; 1-hydroxy-7-aza-benzotriazole; Hoveyda-Grubbs catalyst second generation; dihydrogen peroxide; trimethylaluminum; pivaloyl chloride; titanium tetrachloride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; lithium hydroxide;
In
tetrahydrofuran; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene;
DOI:10.1021/ol301612q
- Guidance literature:
-
Multi-step reaction with 4 steps
1.1: dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; methanol; water / 0 - 20 °C
2.1: 2,6-dimethylpyridine / dichloromethane / 48 h / 0 - 20 °C
2.2: 1.5 h / 20 °C
3.1: 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 0.33 h / 20 °C
3.2: 20 °C
4.1: Hoveyda-Grubbs catalyst second generation / toluene / 12 h / 135 °C
4.2: 24 h / 20 °C
With
2,6-dimethylpyridine; 1-hydroxy-7-aza-benzotriazole; Hoveyda-Grubbs catalyst second generation; dihydrogen peroxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; lithium hydroxide;
In
tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;
DOI:10.1021/ol301612q
