Technology Process of (-)-methyl (1R,2R,3S,5S)-3-(hydroxy)-1,8-dimethyl-8-azabicyclo[3.2.1]octane-2-carboxylate methanesulfonic acid salt
There total 1 articles about (-)-methyl (1R,2R,3S,5S)-3-(hydroxy)-1,8-dimethyl-8-azabicyclo[3.2.1]octane-2-carboxylate methanesulfonic acid salt which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
Multi-step reaction with 11 steps
1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / -78 °C / Inert atmosphere
1.2: 1.25 h / -78 - 20 °C / Inert atmosphere
2.1: dichloromethane / 17 h / 20 °C
3.1: diisobutylaluminium hydride / hexane; dichloromethane / 2 h / -78 °C / Inert atmosphere
4.1: manganese(IV) oxide / dichloromethane / 24 h
5.1: (R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine / chloroform / 41 h / 4 °C
6.1: chloroform / 2 h / 20 °C
7.1: triethylsilane; triethylamine; palladium dichloride / dichloromethane / 8 h / Inert atmosphere; Reflux
8.1: hydrogenchloride; water / tetrahydrofuran / 2 h / 20 °C
9.1: aluminum tri-tert-butoxide / toluene / 68 h / 20 - 150 °C / pressure tube
10.1: benzene / 24 h / 85 °C
11.1: palladium 10% on activated carbon; hydrogen / methanol / 24 h / 20 °C / 2585.81 - 3620.13 Torr
With
hydrogenchloride; triethylsilane; manganese(IV) oxide; oxalyl dichloride; (R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine; palladium 10% on activated carbon; water; hydrogen; diisobutylaluminium hydride; aluminum tri-tert-butoxide; dimethyl sulfoxide; triethylamine; palladium dichloride;
In
tetrahydrofuran; methanol; hexane; dichloromethane; chloroform; toluene; benzene;
2.1: Wittig reaction / 5.1: Michael condensation / 6.1: Wittig reaction / 10.1: sealed pressure tube;
DOI:10.1002/adsc.201100917
- Guidance literature:
-
With
pyridine;
at 20 ℃;
for 20h;
Inert atmosphere;
DOI:10.1021/ol1017118