(3R,4aS,9S,9aR)-7-(benzyloxy)-9-phenyl-3-propyl-1,2,3,4,4a,9,9a,10-octahydroacridine-2,2(1H)-dicarbonitrile

Base Information

Chemical Name:(3R,4aS,9S,9aR)-7-(benzyloxy)-9-phenyl-3-propyl-1,2,3,4,4a,9,9a,10-octahydroacridine-2,2(1H)-dicarbonitrile
CAS No.:1277184-99-2
Molecular Formula:C₃₁H₃₁N₃O
Molecular Weight:461.607
Hs Code.:

Synonyms:(3R,4aS,9S,9aR)-7-(benzyloxy)-9-phenyl-3-propyl-1,2,3,4,4a,9,9a,10-octahydroacridine-2,2(1H)-dicarbonitrile

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Chemical Property of (3R,4aS,9S,9aR)-7-(benzyloxy)-9-phenyl-3-propyl-1,2,3,4,4a,9,9a,10-octahydroacridine-2,2(1H)-dicarbonitrile

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Technology Process of (3R,4aS,9S,9aR)-7-(benzyloxy)-9-phenyl-3-propyl-1,2,3,4,4a,9,9a,10-octahydroacridine-2,2(1H)-dicarbonitrile

There total 1 articles about (3R,4aS,9S,9aR)-7-(benzyloxy)-9-phenyl-3-propyl-1,2,3,4,4a,9,9a,10-octahydroacridine-2,2(1H)-dicarbonitrile 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:

: 6728-26-3
(E)-2-Hexenal

: 6373-46-2
p-benzyloxyaniline

: 219858-21-6
2-[(E)-3-phenyl-2-propenyl]malononitrile

: 7-(benzyloxy)-9-phenyl-3-propyl-1,2,3,4,4a,9,9a,10-octahydroacridine-2,2(1H)-dicarbonitrile

: 1277184-99-2
(3R,4aS,9S,9aR)-7-(benzyloxy)-9-phenyl-3-propyl-1,2,3,4,4a,9,9a,10-octahydroacridine-2,2(1H)-dicarbonitrile

Guidance literature:: (E)-2-Hexenal; 2-[(E)-3-phenyl-2-propenyl]malononitrile; With (S)-2-{bis[3,5-bis(trifluoromethyl)phenyl][(trimethylsilanyl)oxy]methyl}pyrrolidine; benzoic acid; In dichloromethane; at 20 ℃; for 24h;

p-benzyloxyaniline; With trifluoroacetic acid; In dichloromethane; at -30 ℃; for 48h; optical yield given as %ee; enantioselective reaction;
DOI:10.1002/anie.201006608

Reference yield: 94.0%

: 1277184-99-2
(3R,4aS,9S,9aR)-7-(benzyloxy)-9-phenyl-3-propyl-1,2,3,4,4a,9,9a,10-octahydroacridine-2,2(1H)-dicarbonitrile

: 407-25-0
trifluoroacetic anhydride

: 1277185-09-7
(3R,4aS,9S,9aR)-7-benzyloxy-9-phenyl-3-propyl-10-(2,2,2-trifluoroacetyl)-1,2,3,4,4a,9,9a,10-octahydroacridine-2,2(1H)-dicarbonitrile

Guidance literature:: With triethylamine; In dichloromethane; at 20 ℃; for 0.5h;
DOI:10.1002/anie.201006608

Reference yield:

: 1277184-99-2
(3R,4aS,9S,9aR)-7-(benzyloxy)-9-phenyl-3-propyl-1,2,3,4,4a,9,9a,10-octahydroacridine-2,2(1H)-dicarbonitrile

: 1277185-10-0
(3R,4aS,9S,9aR)-7-hydroxy-9-phenyl-3-propyl-10-(2,2,2-trifluoroacetyl)-1,2,3,4,4a,9,9a,10-octahydroacridine-2,2(1H)-dicarbonitrile

Guidance literature:: Multi-step reaction with 2 steps

1: triethylamine / dichloromethane / 0.5 h / 20 °C

2: 20% palladium(II) hydroxide on carbon; hydrogen / ethyl acetate / 24 h / 20 °C / 3750.38 Torr

With 20% palladium(II) hydroxide on carbon; hydrogen; triethylamine; In dichloromethane; ethyl acetate;
DOI:10.1002/anie.201006608