Technology Process of 4-{(2S,4R,5R)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-5-vinyl-piperidin-2-ylmethyl}-6-methoxy-quinoline
There total 14 articles about 4-{(2S,4R,5R)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-5-vinyl-piperidin-2-ylmethyl}-6-methoxy-quinoline 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
sodium tetrahydroborate;
In
tetrahydrofuran; methanol;
at 20 ℃;
for 3h;
DOI:10.1021/ja004325r
- Guidance literature:
-
Multi-step reaction with 9 steps
1.1: 97 percent / xylene / 12 h / Heating
2.1: 3.2 g / diisobutylaluminum hydride / tetrahydrofuran; hexane / 5 h / -78 °C
3.1: 2.54 g / KHMDS / toluene; tetrahydrofuran / 0 - 20 °C
4.1: 95 percent / Ph3P; DEAD; (PhO)2P(O)N3 / tetrahydrofuran / 24 h
5.1: 78 percent / aq. HCl / tetrahydrofuran; CH2Cl2 / 8 h / 20 °C
6.1: LDA / tetrahydrofuran / 0.5 h / -78 - 0 °C
6.2: 72 percent / tetrahydrofuran / 0.58 h / -78 - 0 °C
7.1: 85 percent / DMSO; (ClCO)2; Et3N / CH2Cl2 / 1.5 h / -78 - 20 °C
8.1: 81 percent / Ph3P / tetrahydrofuran / 3 h / Heating
9.1: 91 percent / NaBH4 / methanol; tetrahydrofuran / 3 h / 20 °C
With
hydrogenchloride; sodium tetrahydroborate; oxalyl dichloride; diphenyl phosphoryl azide; potassium hexamethylsilazane; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; triphenylphosphine; lithium diisopropyl amide; diethylazodicarboxylate;
In
tetrahydrofuran; methanol; hexane; dichloromethane; toluene; xylene;
3.1: Wittig reaction / 7.1: Swern oxidation;
DOI:10.1021/ja004325r
- Guidance literature:
-
Multi-step reaction with 10 steps
1.1: 93 percent / PPTS / ethanol / 20 °C
2.1: 97 percent / xylene / 12 h / Heating
3.1: 3.2 g / diisobutylaluminum hydride / tetrahydrofuran; hexane / 5 h / -78 °C
4.1: 2.54 g / KHMDS / toluene; tetrahydrofuran / 0 - 20 °C
5.1: 95 percent / Ph3P; DEAD; (PhO)2P(O)N3 / tetrahydrofuran / 24 h
6.1: 78 percent / aq. HCl / tetrahydrofuran; CH2Cl2 / 8 h / 20 °C
7.1: LDA / tetrahydrofuran / 0.5 h / -78 - 0 °C
7.2: 72 percent / tetrahydrofuran / 0.58 h / -78 - 0 °C
8.1: 85 percent / DMSO; (ClCO)2; Et3N / CH2Cl2 / 1.5 h / -78 - 20 °C
9.1: 81 percent / Ph3P / tetrahydrofuran / 3 h / Heating
10.1: 91 percent / NaBH4 / methanol; tetrahydrofuran / 3 h / 20 °C
With
hydrogenchloride; sodium tetrahydroborate; oxalyl dichloride; diphenyl phosphoryl azide; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; triphenylphosphine; lithium diisopropyl amide; diethylazodicarboxylate;
In
tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; toluene; xylene;
4.1: Wittig reaction / 8.1: Swern oxidation;
DOI:10.1021/ja004325r
![4-{(4R,5R)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-5-vinyl-3,4,5,6-tetrahydro-pyridin-2-ylmethyl}-6-methoxy-quinoline](/Databaselist/images/loading.webp)
