4-{(2S,4R,5R)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-5-vinyl-piperidin-2-ylmethyl}-6-methoxy-quinoline

Base Information

Chemical Name:4-{(2S,4R,5R)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-5-vinyl-piperidin-2-ylmethyl}-6-methoxy-quinoline
CAS No.:339046-95-6
Molecular Formula:C₃₆H₄₄N₂O₂Si
Molecular Weight:564.843
Hs Code.:

Synonyms:4-{(2S,4R,5R)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-5-vinyl-piperidin-2-ylmethyl}-6-methoxy-quinoline

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Chemical Property of 4-{(2S,4R,5R)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-5-vinyl-piperidin-2-ylmethyl}-6-methoxy-quinoline

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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:

Reference yield: 91.0%

: 339046-94-5
4-{(4R,5R)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-5-vinyl-3,4,5,6-tetrahydro-pyridin-2-ylmethyl}-6-methoxy-quinoline

: 339046-95-6
4-{(2S,4R,5R)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-5-vinyl-piperidin-2-ylmethyl}-6-methoxy-quinoline

Guidance literature:: With sodium tetrahydroborate; In tetrahydrofuran; methanol; at 20 ℃; for 3h;
DOI:10.1021/ja004325r

Reference yield:

: 339046-98-9
(2R,3R)-2-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-3-hydroxymethyl-pent-4-enoic acid diethylamide

: 339046-95-6
4-{(2S,4R,5R)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-5-vinyl-piperidin-2-ylmethyl}-6-methoxy-quinoline

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

Reference yield:

: 339046-87-6
3-(tert-butyl-dimethyl-silanyloxymethyl)-2-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-pent-4-enoic acid diethylamide

: 339046-95-6
4-{(2S,4R,5R)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-5-vinyl-piperidin-2-ylmethyl}-6-methoxy-quinoline

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