Technology Process of (1S,3R,4S)-3-[(4'-methoxyphenyl)methoxy]bicyclo[2.2.2]octan-2,5-dione 5-(ethylene acetal)
There total 9 articles about (1S,3R,4S)-3-[(4'-methoxyphenyl)methoxy]bicyclo[2.2.2]octan-2,5-dione 5-(ethylene acetal) 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:
- Guidance literature:
-
With
oxalyl dichloride; dimethyl sulfoxide; triethylamine;
In
dichloromethane;
at -78 - 18 ℃;
for 1h;
DOI:10.1039/b105376k
- Guidance literature:
-
Multi-step reaction with 8 steps
1: 14.1 g / (1S)-(+)-camphor-10-sulfonic acid monohydrate / CH2Cl2 / 1 h / -20 - 10 °C
2: 91 percent / TMSOTf / CH2Cl2 / 24 h / 18 °C
3: 97 percent / H2 / 10 percent Pd/C / tetrahydrofuran / 26 h / 18 °C
4: 97 percent / (1S)-(+)-camphor-10-sulfonic acid monohydrate / CH2Cl2 / 3 h / -20 °C
5: 70 percent / DIBAL-H / CH2Cl2; hexane / 10 h / -50 - 0 °C
6: 70 percent / Bu3SnH; AIBN / benzene / 6 h / 18 °C / Irradiation
7: 96 percent / (COCl)2; DMSO; Et3N / CH2Cl2 / 1 h / -78 - 18 °C
With
oxalyl dichloride; 2,2'-azobis(isobutyronitrile); trimethylsilyl trifluoromethanesulfonate; (+)-camphor-10-sulfonic acid monohydrate; hydrogen; tri-n-butyl-tin hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine;
palladium on activated charcoal;
In
tetrahydrofuran; hexane; dichloromethane; benzene;
DOI:10.1039/b105376k
- Guidance literature:
-
Multi-step reaction with 7 steps
1: 91 percent / TMSOTf / CH2Cl2 / 24 h / 18 °C
2: 97 percent / H2 / 10 percent Pd/C / tetrahydrofuran / 26 h / 18 °C
3: 97 percent / (1S)-(+)-camphor-10-sulfonic acid monohydrate / CH2Cl2 / 3 h / -20 °C
4: 70 percent / DIBAL-H / CH2Cl2; hexane / 10 h / -50 - 0 °C
5: 70 percent / Bu3SnH; AIBN / benzene / 6 h / 18 °C / Irradiation
6: 96 percent / (COCl)2; DMSO; Et3N / CH2Cl2 / 1 h / -78 - 18 °C
With
oxalyl dichloride; 2,2'-azobis(isobutyronitrile); trimethylsilyl trifluoromethanesulfonate; (+)-camphor-10-sulfonic acid monohydrate; hydrogen; tri-n-butyl-tin hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine;
palladium on activated charcoal;
In
tetrahydrofuran; hexane; dichloromethane; benzene;
DOI:10.1039/b105376k
![(1S,4S,5S,6R)-5-hydroxy-6-[(4'-methoxyphenyl)methoxy]bicyclo[2.2.2]octan-2-one ethylene acetal](/Databaselist/images/loading.webp)
