(4R,12bS)-4-(furan-2-yl)-12-tosyl-1,3,4,6,7,12b-hexahydroindolo[2,3-a]quinolizin-2(12H)-one

Base Information

Chemical Name:(4R,12bS)-4-(furan-2-yl)-12-tosyl-1,3,4,6,7,12b-hexahydroindolo[2,3-a]quinolizin-2(12H)-one
CAS No.:1421697-22-4
Molecular Formula:C₂₆H₂₄N₂O₄S
Molecular Weight:460.554
Hs Code.:

Synonyms:(4R,12bS)-4-(furan-2-yl)-12-tosyl-1,3,4,6,7,12b-hexahydroindolo[2,3-a]quinolizin-2(12H)-one

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Chemical Property of (4R,12bS)-4-(furan-2-yl)-12-tosyl-1,3,4,6,7,12b-hexahydroindolo[2,3-a]quinolizin-2(12H)-one

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Technology Process of (4R,12bS)-4-(furan-2-yl)-12-tosyl-1,3,4,6,7,12b-hexahydroindolo[2,3-a]quinolizin-2(12H)-one

There total 5 articles about (4R,12bS)-4-(furan-2-yl)-12-tosyl-1,3,4,6,7,12b-hexahydroindolo[2,3-a]quinolizin-2(12H)-one 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: 84.0%

: 623-15-4
(E)-4-(furan-2-yl)but-3-en-2-one

: 145865-96-9
4,9-dihydro-9-(p-toluenesulfonyl)-3H-pyrido-<3,4-b>indole

: 1421697-07-5
(4S,12bS)-4-(furan-2-yl)-12-tosyl-1,3,4,6,7,12b-hexahydroindolo[2,3-a]quinolizin-2(12H)-one

: 1421697-22-4
(4R,12bS)-4-(furan-2-yl)-12-tosyl-1,3,4,6,7,12b-hexahydroindolo[2,3-a]quinolizin-2(12H)-one

Guidance literature:: With (S)-2-(3-((1R,2R)-2-aminocyclohexyl)thioureido)-N-benzhydryl-N,3,3-trimethylbutanamide; acetic acid; In toluene; at 4 ℃; for 48h; enantioselective reaction; Inert atmosphere;
DOI:10.1021/ja310718f

Reference yield:

: 869096-24-2
9-tolylsulfonyl-4,9-dihydro-3H-β-carboline

: 623-15-4
(E)-4-(furan-2-yl)but-3-en-2-one

: 1669-43-8,5166-53-0,1821-29-0
(E)-4-isopropylbut-3-en-2-one

: 1421697-22-4
(4R,12bS)-4-(furan-2-yl)-12-tosyl-1,3,4,6,7,12b-hexahydroindolo[2,3-a]quinolizin-2(12H)-one

Guidance literature:: 9-tolylsulfonyl-4,9-dihydro-3H-β-carboline; (E)-4-(furan-2-yl)but-3-en-2-one; With tris(triphenylphosphine)ruthenium(II) chloride; (S)-2-(3-((1R,2R)-2-aminocyclohexyl)thioureido)-N-benzhydryl-N,3,3-trimethylbutanamide; acetic acid; In toluene; at 0 - 20 ℃; for 0.166667h;

With tert.-butylhydroperoxide; In decane; toluene; at 0 ℃; for 48.75h; Overall yield = 42 %; enantioselective reaction;
DOI:10.3390/molecules23092228

Reference yield:

: 61-54-1
tryptamine

: 1421697-07-5
(4S,12bS)-4-(furan-2-yl)-12-tosyl-1,3,4,6,7,12b-hexahydroindolo[2,3-a]quinolizin-2(12H)-one

: 1421697-22-4
(4R,12bS)-4-(furan-2-yl)-12-tosyl-1,3,4,6,7,12b-hexahydroindolo[2,3-a]quinolizin-2(12H)-one

Guidance literature:: Multi-step reaction with 4 steps

1: triethylamine / methanol / 16 h / 100 °C / Inert atmosphere

2: trichlorophosphate / acetonitrile / 3 h / 0 °C / Inert atmosphere

3: caesium carbonate / N,N-dimethyl-formamide / 48 h / 23 °C / Inert atmosphere

4: acetic acid; (S)-2-(3-((1R,2R)-2-aminocyclohexyl)thioureido)-N-benzhydryl-N,3,3-trimethylbutanamide / toluene / 48 h / 4 °C / Inert atmosphere

With (S)-2-(3-((1R,2R)-2-aminocyclohexyl)thioureido)-N-benzhydryl-N,3,3-trimethylbutanamide; caesium carbonate; acetic acid; triethylamine; trichlorophosphate; In methanol; N,N-dimethyl-formamide; toluene; acetonitrile; 4: |Diels-Alder Cycloaddition;
DOI:10.1021/ja310718f