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

Base Information

Chemical Name: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
CAS No.:75685-52-8
Molecular Formula:C₃₂H₄₇NO₂Si
Molecular Weight:505.816
Hs Code.:

Synonyms: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

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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-(2-hydroxyethyl)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-(2-hydroxyethyl)pyrrolo<1,2-a>quinoline

There total 45 articles about 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 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: 86.0%

: 86197-21-9
(1S,3aS,5aS,6S,9aR)-1-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-6-(2-methoxymethoxy-ethyl)-dodecahydro-pyrrolo[1,2-a]quinoline

: 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

Guidance literature:: With hydrogen bromide; In 1,2-dimethoxyethane; at 50 ℃; for 2h;
DOI:10.1021/ja00354a031

Reference yield:

: 6102-41-6,6102-44-9,14116-78-0,70749-10-9,70749-11-0,78341-47-6
rel-(4aS,8aS)-1,2,3,4,4a,5,8,8a-octahydronaphthalen-2-one

: 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

Guidance literature:: Multi-step reaction with 14 steps

1: 83 percent / lithium aluminum hydride / tetrahydrofuran / 1.) -70 deg C, 75 min, 2.) 3 h

2: 62 percent / triphenylphosphine, diethyl azodicarboxylate / tetrahydrofuran / 1.) 0 deg C, 45 min, 2.) room temperature, 30 min

3: 1.) ozone, 2.) sodium borohydride / methanol / 1.) -78 deg C, 43 min

4: 1.) o-nitrophenyl selenocyanate, tri-n-butylphosphine, 2.) aq. hydrogen peroxide / 1.) THF, 0 deg C, 15 min; room temperature, 45 min, 2.) 0 deg C, 20 min; 30 min

5: 80 percent / diisobutylaluminum hydride / toluene / -70 - -65 °C

6: 1 percent / CH₂Cl₂ / 1.) 0 deg C, 15 min, 2.) 30 min

8: 68 percent / tri-n-butyltin hydride / toluene / 16.75 h / Heating

9: 95 percent / Lawesson's reagent / toluene / 10 h / 100 °C

10: 2.) triphenylphosphine, triethylamine / 1.) ether, room temperature, 46 h, 2.) dichloromethane, 0 deg C, 15 min

11: 59 percent / bromocresol green, sodium cyanoborohydride, hydrochloric acid, pH 4 / methanol / 0.5 h

12: 90 percent / lithium aluminum hydride / tetrahydrofuran / 1 h / Ambient temperature

13: 100 percent / imidazole / dimethylformamide / 36 h / Ambient temperature

14: 1.) disiamylborane, 2.) aq. sodium hydroxide, aq. hydrogen peroxide / 1.) THF, 0 deg C, 30 min, 2.) room temperature, 30 min

With Lawessons reagent; 1H-imidazole; hydrogenchloride; sodium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; ortho-nitrophenyl selenocyanate; tributylphosphine; dihydrogen peroxide; tri-n-butyl-tin hydride; bromocresol green; bis-(1,2-dimethylpropyl)borane; diisobutylaluminium hydride; sodium cyanoborohydride; ozone; triethylamine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/ja00343a030

Reference yield:

: 78308-03-9
N-succinimide

: 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

Guidance literature:: Multi-step reaction with 10 steps

1: 80 percent / diisobutylaluminum hydride / toluene / -70 - -65 °C

2: 1 percent / CH₂Cl₂ / 1.) 0 deg C, 15 min, 2.) 30 min

4: 68 percent / tri-n-butyltin hydride / toluene / 16.75 h / Heating

5: 95 percent / Lawesson's reagent / toluene / 10 h / 100 °C

6: 2.) triphenylphosphine, triethylamine / 1.) ether, room temperature, 46 h, 2.) dichloromethane, 0 deg C, 15 min

7: 59 percent / bromocresol green, sodium cyanoborohydride, hydrochloric acid, pH 4 / methanol / 0.5 h

8: 90 percent / lithium aluminum hydride / tetrahydrofuran / 1 h / Ambient temperature

9: 100 percent / imidazole / dimethylformamide / 36 h / Ambient temperature

10: 1.) disiamylborane, 2.) aq. sodium hydroxide, aq. hydrogen peroxide / 1.) THF, 0 deg C, 30 min, 2.) room temperature, 30 min

With Lawessons reagent; 1H-imidazole; hydrogenchloride; sodium hydroxide; lithium aluminium tetrahydride; dihydrogen peroxide; tri-n-butyl-tin hydride; bromocresol green; bis-(1,2-dimethylpropyl)borane; diisobutylaluminium hydride; sodium cyanoborohydride; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/ja00343a030