1α,2,3,3aα,4,5,5aβ,6α,7,8,9,9aβ-dodecahydro-1-<2-<(tert-butyldiphenylsilyl)oxy>ethyl>-6-<5-(triiisopropylsilyl)-2(Z)-penten-4-ynyl>pyrrolo<1,2-a>quinoline

Base Information

Chemical Name:1α,2,3,3aα,4,5,5aβ,6α,7,8,9,9aβ-dodecahydro-1-<2-<(tert-butyldiphenylsilyl)oxy>ethyl>-6-<5-(triiisopropylsilyl)-2(Z)-penten-4-ynyl>pyrrolo<1,2-a>quinoline
CAS No.:86197-22-0
Molecular Formula:C₄₄H₆₇NOSi₂
Molecular Weight:682.193
Hs Code.:

1α,2,3,3aα,4,5,5aβ,6α,7,8,9,9aβ-dodecahydro-1-<2-<(tert-butyldiphenylsilyl)oxy>ethyl>-6-<5-(triiisopropylsilyl)-2(Z)-penten-4-ynyl>pyrrolo<1,2-a>quinoline

Synonyms:1α,2,3,3aα,4,5,5aβ,6α,7,8,9,9aβ-dodecahydro-1-<2-<(tert-butyldiphenylsilyl)oxy>ethyl>-6-<5-(triiisopropylsilyl)-2(Z)-penten-4-ynyl>pyrrolo<1,2-a>quinoline

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Chemical Property of 1α,2,3,3aα,4,5,5aβ,6α,7,8,9,9aβ-dodecahydro-1-<2-<(tert-butyldiphenylsilyl)oxy>ethyl>-6-<5-(triiisopropylsilyl)-2(Z)-penten-4-ynyl>pyrrolo<1,2-a>quinoline

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Technology Process of 1α,2,3,3aα,4,5,5aβ,6α,7,8,9,9aβ-dodecahydro-1-<2-<(tert-butyldiphenylsilyl)oxy>ethyl>-6-<5-(triiisopropylsilyl)-2(Z)-penten-4-ynyl>pyrrolo<1,2-a>quinoline

There total 10 articles about 1α,2,3,3aα,4,5,5aβ,6α,7,8,9,9aβ-dodecahydro-1-<2-<(tert-butyldiphenylsilyl)oxy>ethyl>-6-<5-(triiisopropylsilyl)-2(Z)-penten-4-ynyl>pyrrolo<1,2-a>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: 55.0%

: 82192-59-4
1,3-bis(triisopropylsilyl)prop-1-yne

: 75648-76-9
{(1S,3aS,5aS,6S,9aR)-1-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-dodecahydro-pyrrolo[1,2-a]quinolin-6-yl}-acetaldehyde

: 86197-22-0
1α,2,3,3aα,4,5,5aβ,6α,7,8,9,9aβ-dodecahydro-1-<2-<(tert-butyldiphenylsilyl)oxy>ethyl>-6-<5-(triiisopropylsilyl)-2(Z)-penten-4-ynyl>pyrrolo<1,2-a>quinoline

: 86258-59-5
1α,2,3,3aα,4,5,5aβ,6α,7,8,9,9aβ-dodecahydro-1-<2-<(tert-butyldiphenylsilyl)oxy>ethyl>-6-<5-(triiisopropylsilyl)-2(E)-penten-4-ynyl>pyrrolo<1,2-a>quinoline

Guidance literature:: With n-butyllithium; In tetrahydrofuran; hexane; 1.) -20 deg C, 15 min, 2.) -78 deg C -> RT, 12 h;
DOI:10.1021/ja00354a031

Reference yield:

: 75685-52-8
1α,2,3,3aα,4,5,5aβ,6α,7,8,9,9aβ-dodecahydro-1-<2-<(tert-butyldiphenylsilyl)oxy>ethyl>-6-(2-hydroxyethyl)pyrrolo<1,2-a>quinoline

: 86197-22-0
1α,2,3,3aα,4,5,5aβ,6α,7,8,9,9aβ-dodecahydro-1-<2-<(tert-butyldiphenylsilyl)oxy>ethyl>-6-<5-(triiisopropylsilyl)-2(Z)-penten-4-ynyl>pyrrolo<1,2-a>quinoline

Guidance literature:: Multi-step reaction with 2 steps

1: 100 percent / oxalyl chloride / dimethylsulfoxide

2: 55 percent / BuLi / tetrahydrofuran; hexane / 1.) -20 deg C, 15 min, 2.) -78 deg C -> RT, 12 h

With n-butyllithium; oxalyl dichloride; In tetrahydrofuran; hexane; dimethyl sulfoxide;
DOI:10.1021/ja00354a031

Reference yield:

: 86197-25-3
(2S,4aS,5S,8aR)-5-(2-Methoxymethoxy-ethyl)-2-(3-oxo-propyl)-octahydro-quinoline-1-carboxylic acid 2,2,2-trichloro-ethyl ester

: 86197-22-0
1α,2,3,3aα,4,5,5aβ,6α,7,8,9,9aβ-dodecahydro-1-<2-<(tert-butyldiphenylsilyl)oxy>ethyl>-6-<5-(triiisopropylsilyl)-2(Z)-penten-4-ynyl>pyrrolo<1,2-a>quinoline

Guidance literature:: Multi-step reaction with 8 steps

1: CHCl₃ / 81 h / Heating

2: 98 percent / pyridinium p-toluenesulfonate / 1 h

3: KOH / propan-2-ol; H₂O / 48 h / Heating

4: 1.) 1 N HCl, 2.) MeONa, 3.) NaBH₄ / 1.) THF, RT, 1 h, 2.) MeOH-THF, RT, 1 h, 3.) RT, 0.5 h

5: 83 percent / Et₃N, 4-(dimethylamino)pyridine / CH₂Cl₂ / Ambient temperature

6: 86 percent / 24percent aq. HBr / 1,2-dimethoxy-ethane / 2 h / 50 °C

7: 100 percent / oxalyl chloride / dimethylsulfoxide

8: 55 percent / BuLi / tetrahydrofuran; hexane / 1.) -20 deg C, 15 min, 2.) -78 deg C -> RT, 12 h

With hydrogenchloride; dmap; potassium hydroxide; sodium tetrahydroborate; n-butyllithium; oxalyl dichloride; hydrogen bromide; sodium methylate; pyridinium p-toluenesulfonate; triethylamine; In tetrahydrofuran; 1,2-dimethoxyethane; hexane; dichloromethane; chloroform; water; dimethyl sulfoxide; isopropyl alcohol;
DOI:10.1021/ja00354a031