rel-(3aS,5aS,6S,9aR)-1(E)-(carbethoxymethylidene)-6-((2-tert-butyldiphenylsiloxy)ethyl)dodecahydropyrrolo<1,2-a>quinoline

Base Information

Chemical Name:rel-(3aS,5aS,6S,9aR)-1(E)-(carbethoxymethylidene)-6-((2-tert-butyldiphenylsiloxy)ethyl)dodecahydropyrrolo<1,2-a>quinoline
CAS No.:84175-96-2
Molecular Formula:C₃₄H₄₇NO₃Si
Molecular Weight:545.838
Hs Code.:

Synonyms:rel-(3aS,5aS,6S,9aR)-1(E)-(carbethoxymethylidene)-6-((2-tert-butyldiphenylsiloxy)ethyl)dodecahydropyrrolo<1,2-a>quinoline

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Chemical Property of rel-(3aS,5aS,6S,9aR)-1(E)-(carbethoxymethylidene)-6-((2-tert-butyldiphenylsiloxy)ethyl)dodecahydropyrrolo<1,2-a>quinoline

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Technology Process of rel-(3aS,5aS,6S,9aR)-1(E)-(carbethoxymethylidene)-6-((2-tert-butyldiphenylsiloxy)ethyl)dodecahydropyrrolo<1,2-a>quinoline

There total 15 articles about rel-(3aS,5aS,6S,9aR)-1(E)-(carbethoxymethylidene)-6-((2-tert-butyldiphenylsiloxy)ethyl)dodecahydropyrrolo<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: 95.0%

: 84175-95-1
rel-(3aS,5aS,6S,9aR)-1(E)-(carbethoxymethylidene)-6-(2-hydroxyethyl)dodecahydropyrrolo<1,2-a>quinoline

: 58479-61-1
tert-butylchlorodiphenylsilane

: 84175-96-2
rel-(3aS,5aS,6S,9aR)-1(E)-(carbethoxymethylidene)-6-((2-tert-butyldiphenylsiloxy)ethyl)dodecahydropyrrolo<1,2-a>quinoline

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; for 60h; Ambient temperature;
DOI:10.1021/ja00343a030

Reference yield:

: 930-68-7
cyclohexenone

: 84175-96-2
rel-(3aS,5aS,6S,9aR)-1(E)-(carbethoxymethylidene)-6-((2-tert-butyldiphenylsiloxy)ethyl)dodecahydropyrrolo<1,2-a>quinoline

Guidance literature:: Multi-step reaction with 13 steps

1: 70 percent / 1.) aluminum chloride / benzene / 1.) room temperature, 45 min, 2.) 70-75 deg C, 5 h

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

3: 62 percent / triphenylphosphine, diethyl azodicarboxylate / tetrahydrofuran / 1.) 0 deg C, 45 min, 2.) room temperature, 30 min

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

5: 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

6: 80 percent / diisobutylaluminum hydride / toluene / -70 - -65 °C

7: 1 percent / CH₂Cl₂ / 1.) 0 deg C, 15 min, 2.) 30 min

9: 68 percent / tri-n-butyltin hydride / toluene / 16.75 h / Heating

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

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

12: 1.) disiamylborane, 2.) aq. sodium hydroxide, aq. hydrogen peroxide / 1.) THF, 0 deg C, 50 min, 2.) room temperature, 30 min

13: 95 percent / imidazole / dimethylformamide / 60 h / Ambient temperature

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

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

: 84175-96-2
rel-(3aS,5aS,6S,9aR)-1(E)-(carbethoxymethylidene)-6-((2-tert-butyldiphenylsiloxy)ethyl)dodecahydropyrrolo<1,2-a>quinoline

Guidance literature:: Multi-step reaction with 12 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: 1.) disiamylborane, 2.) aq. sodium hydroxide, aq. hydrogen peroxide / 1.) THF, 0 deg C, 50 min, 2.) room temperature, 30 min

12: 95 percent / imidazole / dimethylformamide / 60 h / Ambient temperature

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