(2R,6S,12bS,13R)-3-Eth-(E)-ylidene-12-methyl-13-triisopropylsilanyloxymethyl-1,3,4,7,12,12b-hexahydro-2H,6H-2,6-methano-indolo[2,3-a]quinolizine

Base Information

Chemical Name:(2R,6S,12bS,13R)-3-Eth-(E)-ylidene-12-methyl-13-triisopropylsilanyloxymethyl-1,3,4,7,12,12b-hexahydro-2H,6H-2,6-methano-indolo[2,3-a]quinolizine
CAS No.:391623-78-2
Molecular Formula:C₂₉H₄₄N₂OSi
Molecular Weight:464.767
Hs Code.:

Synonyms:(2R,6S,12bS,13R)-3-Eth-(E)-ylidene-12-methyl-13-triisopropylsilanyloxymethyl-1,3,4,7,12,12b-hexahydro-2H,6H-2,6-methano-indolo[2,3-a]quinolizine

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Chemical Property of (2R,6S,12bS,13R)-3-Eth-(E)-ylidene-12-methyl-13-triisopropylsilanyloxymethyl-1,3,4,7,12,12b-hexahydro-2H,6H-2,6-methano-indolo[2,3-a]quinolizine

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Technology Process of (2R,6S,12bS,13R)-3-Eth-(E)-ylidene-12-methyl-13-triisopropylsilanyloxymethyl-1,3,4,7,12,12b-hexahydro-2H,6H-2,6-methano-indolo[2,3-a]quinolizine

There total 1 articles about (2R,6S,12bS,13R)-3-Eth-(E)-ylidene-12-methyl-13-triisopropylsilanyloxymethyl-1,3,4,7,12,12b-hexahydro-2H,6H-2,6-methano-indolo[2,3-a]quinolizine 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: 90.0%

: 80522-42-5
triisopropylsilyl trifluoromethanesulfonate

: 2912-11-0
(+)-affinisine

: 391623-78-2
(2R,6S,12bS,13R)-3-Eth-(E)-ylidene-12-methyl-13-triisopropylsilanyloxymethyl-1,3,4,7,12,12b-hexahydro-2H,6H-2,6-methano-indolo[2,3-a]quinolizine

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at 0 ℃; for 2h;
DOI:10.1021/jo061652u

Reference yield:

: 391623-78-2
(2R,6S,12bS,13R)-3-Eth-(E)-ylidene-12-methyl-13-triisopropylsilanyloxymethyl-1,3,4,7,12,12b-hexahydro-2H,6H-2,6-methano-indolo[2,3-a]quinolizine

: 2269-93-4
(+)-macroline

Guidance literature:: Multi-step reaction with 4 steps

1.1: BH₃*Me₂S / tetrahydrofuran / 3 h / 20 °C

1.2: aq. NaOH; aq. H₂O₂ / tetrahydrofuran / 2 h / 20 °C

1.3: 95 percent / HOAc / tetrahydrofuran / 5 h / Heating

2.1: 82 percent / Dess-Martin periodinane / CH₂Cl₂ / 4 h / 0 °C

3.1: tetrahydrofuran / 0 °C

3.2: 90 percent / t-BuOK / ethanol; tetrahydrofuran / 2 h / Heating

4.1: 86 percent / TBAF*H₂O / tetrahydrofuran / 4 h / 20 °C

With dimethylsulfide borane complex; tetrabutyl ammonium fluoride; Dess-Martin periodane; In tetrahydrofuran; dichloromethane; 2.1: Dess-Martin oxidation;
DOI:10.1021/jo061652u

Reference yield:

: 391623-78-2
(2R,6S,12bS,13R)-3-Eth-(E)-ylidene-12-methyl-13-triisopropylsilanyloxymethyl-1,3,4,7,12,12b-hexahydro-2H,6H-2,6-methano-indolo[2,3-a]quinolizine

: 25921-22-6
alstonerine

Guidance literature:: Multi-step reaction with 4 steps

1.1: BH₃*Me₂S / tetrahydrofuran / 3 h / 20 °C

1.2: aq. NaOH; aq. H₂O₂ / tetrahydrofuran / 2 h / 20 °C

1.3: 95 percent / HOAc / tetrahydrofuran / 5 h / Heating

2.1: 82 percent / Dess-Martin periodinane / CH₂Cl₂ / 4 h / 0 °C

3.1: tetrahydrofuran / 0 °C

3.2: 90 percent / t-BuOK / ethanol; tetrahydrofuran / 2 h / Heating

4.1: 60 percent / Na₂PdCl₄; t-BuOOH; aq. AcOH / 2-methyl-propan-2-ol / 5 h / 80 °C

With tert.-butylhydroperoxide; sodium tetrachloropalladate(II); dimethylsulfide borane complex; Dess-Martin periodane; acetic acid; In tetrahydrofuran; dichloromethane; tert-butyl alcohol; 2.1: Dess-Martin oxidation;
DOI:10.1021/jo061652u