Technology Process of (1R,4S,7S)-4-((tert-butyldiphenylsilyloxy)methyl)-3-tosyl-8-oxa-3-azabicyclo[5.1.0]octane
There total 7 articles about (1R,4S,7S)-4-((tert-butyldiphenylsilyloxy)methyl)-3-tosyl-8-oxa-3-azabicyclo[5.1.0]octane which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
Multi-step reaction with 4 steps
1.1: 1H-imidazole / N,N-dimethyl-formamide / 24.08 h / 20 °C / Inert atmosphere
2.1: n-butyllithium; hexamethyldisilazide / tetrahydrofuran; hexane / 1 h / -20 °C / Inert atmosphere
2.2: -20 - 20 °C / Inert atmosphere
3.1: diisobutylaluminium hydride / dichloromethane / -78 - 20 °C / Inert atmosphere
4.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / N,N-dimethyl-formamide / 0.17 h / 0 °C / Inert atmosphere
4.2: 15 h / 0 - 20 °C / Inert atmosphere
With
1H-imidazole; n-butyllithium; hexamethyldisilazide; diisobutylaluminium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene;
In
tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1002/asia.201000817
- Guidance literature:
-
N-p-toluenesulphonyl(5-diphenyl-tert-butylsilyloxymethyl)-2-hydroxypyrrolidine;
With
1,8-diazabicyclo[5.4.0]undec-7-ene;
In
N,N-dimethyl-formamide;
at 0 ℃;
for 0.166667h;
Inert atmosphere;
diphenyl(vinyl)sulfonium trifluoromethanesulfonate;
In
N,N-dimethyl-formamide;
at 0 - 20 ℃;
for 15h;
optical yield given as %de;
diastereoselective reaction;
Inert atmosphere;
DOI:10.1002/asia.201000817
- Guidance literature:
-
Multi-step reaction with 5 steps
1.1: sodium tetrahydroborate / ethanol / 2 h / 20 °C / Inert atmosphere; Cooling with ice
2.1: 1H-imidazole / N,N-dimethyl-formamide / 24.08 h / 20 °C / Inert atmosphere
3.1: n-butyllithium; hexamethyldisilazide / tetrahydrofuran; hexane / 1 h / -20 °C / Inert atmosphere
3.2: -20 - 20 °C / Inert atmosphere
4.1: diisobutylaluminium hydride / dichloromethane / -78 - 20 °C / Inert atmosphere
5.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / N,N-dimethyl-formamide / 0.17 h / 0 °C / Inert atmosphere
5.2: 15 h / 0 - 20 °C / Inert atmosphere
With
1H-imidazole; sodium tetrahydroborate; n-butyllithium; hexamethyldisilazide; diisobutylaluminium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene;
In
tetrahydrofuran; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1002/asia.201000817
