(2R,3S,12bR)-methyl 1,2,3,4,6,7,12,12b-octahydro-4-oxo-2-phenylindolo[2,3-a]quinolizine-3-carboxylate

Base Information

Chemical Name:(2R,3S,12bR)-methyl 1,2,3,4,6,7,12,12b-octahydro-4-oxo-2-phenylindolo[2,3-a]quinolizine-3-carboxylate
CAS No.:1133909-62-2
Molecular Formula:C₂₃H₂₂N₂O₃
Molecular Weight:374.439
Hs Code.:

Synonyms:(2R,3S,12bR)-methyl 1,2,3,4,6,7,12,12b-octahydro-4-oxo-2-phenylindolo[2,3-a]quinolizine-3-carboxylate

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Chemical Property of (2R,3S,12bR)-methyl 1,2,3,4,6,7,12,12b-octahydro-4-oxo-2-phenylindolo[2,3-a]quinolizine-3-carboxylate

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Technology Process of (2R,3S,12bR)-methyl 1,2,3,4,6,7,12,12b-octahydro-4-oxo-2-phenylindolo[2,3-a]quinolizine-3-carboxylate

There total 4 articles about (2R,3S,12bR)-methyl 1,2,3,4,6,7,12,12b-octahydro-4-oxo-2-phenylindolo[2,3-a]quinolizine-3-carboxylate 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%

: 908303-06-0
(R)-2-(3-oxo-1-phenylpropyl)malonic acid dimethyl ester

: 61-54-1
tryptamine

: 1133909-62-2
(2R,3S,12bR)-methyl 1,2,3,4,6,7,12,12b-octahydro-4-oxo-2-phenylindolo[2,3-a]quinolizine-3-carboxylate

Guidance literature:: (R)-2-(3-oxo-1-phenylpropyl)malonic acid dimethyl ester; tryptamine; With trifluoroacetic acid; In dichloromethane; at 50 ℃; for 12h;

With sodium hydrogencarbonate; In dichloromethane; optical yield given as %ee; enantioselective reaction;
DOI:10.1021/ol101922h

Reference yield:

: C₂₃H₂₄N₂O₄

: 1133909-61-1
(2R,3S,12bS)-methyl 1,2,3,4,6,7,12,12b-octahydro-4-oxo-2-phenylindolo[2,3-a]quinolizine-3-carboxylate

: 1133909-62-2
(2R,3S,12bR)-methyl 1,2,3,4,6,7,12,12b-octahydro-4-oxo-2-phenylindolo[2,3-a]quinolizine-3-carboxylate

Guidance literature:: With hydrogenchloride; In diethyl ether; dichloromethane; at -78 - 20 ℃; optical yield given as %de; diastereoselective reaction;
DOI:10.1002/anie.200805130

Reference yield:

: 104-55-2
3-phenyl-propenal

: 1133909-62-2
(2R,3S,12bR)-methyl 1,2,3,4,6,7,12,12b-octahydro-4-oxo-2-phenylindolo[2,3-a]quinolizine-3-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1: (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine / ethanol / 48 h / 0 °C

2: trifluoroacetic acid / dichloromethane / 12 h / 50 °C

With (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine; trifluoroacetic acid; In ethanol; dichloromethane; 1: Michael addition;
DOI:10.1021/ol101922h