(3S,11bS)-9,11-bis(benzyloxy)-3-(dibenzylamino)-2,3,6,7-tetrahydro-1H-pyrido[2,1-a]isoquinolin-4(11bH)-one

Base Information

Chemical Name:(3S,11bS)-9,11-bis(benzyloxy)-3-(dibenzylamino)-2,3,6,7-tetrahydro-1H-pyrido[2,1-a]isoquinolin-4(11bH)-one
CAS No.:1327254-72-7
Molecular Formula:C₄₁H₄₀N₂O₃
Molecular Weight:608.78
Hs Code.:

Synonyms:(3S,11bS)-9,11-bis(benzyloxy)-3-(dibenzylamino)-2,3,6,7-tetrahydro-1H-pyrido[2,1-a]isoquinolin-4(11bH)-one

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Chemical Property of (3S,11bS)-9,11-bis(benzyloxy)-3-(dibenzylamino)-2,3,6,7-tetrahydro-1H-pyrido[2,1-a]isoquinolin-4(11bH)-one

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Technology Process of (3S,11bS)-9,11-bis(benzyloxy)-3-(dibenzylamino)-2,3,6,7-tetrahydro-1H-pyrido[2,1-a]isoquinolin-4(11bH)-one

There total 9 articles about (3S,11bS)-9,11-bis(benzyloxy)-3-(dibenzylamino)-2,3,6,7-tetrahydro-1H-pyrido[2,1-a]isoquinolin-4(11bH)-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: 46.0%

: 1327254-59-0
(3S)-1-[3,5-bis(benzyloxy)phenethyl]-3-(dibenzylamino)-6-hydroxypiperidin-2-one

: 1327254-73-8
(S)-1-(3,5-bis(benzyloxy)phenethyl)-3-(dibenzylamino)-3,4-dihydropyridin-2(1H)-one

: 1327254-72-7
(3S,11bS)-9,11-bis(benzyloxy)-3-(dibenzylamino)-2,3,6,7-tetrahydro-1H-pyrido[2,1-a]isoquinolin-4(11bH)-one

: (3S,11bR)-9,11-bis(benzyloxy)-3-(dibenzylamino)-2,3,6,7-tetrahydro-1H-pyrido[2,1-a]isoquinolin-4(11bH)-one

Guidance literature:: With acetic acid; In dichloromethane; at 20 ℃; for 48h;
DOI:10.1016/j.tet.2011.06.023

Reference yield:

: 1327254-59-0
(3S)-1-[3,5-bis(benzyloxy)phenethyl]-3-(dibenzylamino)-6-hydroxypiperidin-2-one

: 1327254-72-7
(3S,11bS)-9,11-bis(benzyloxy)-3-(dibenzylamino)-2,3,6,7-tetrahydro-1H-pyrido[2,1-a]isoquinolin-4(11bH)-one

: (3S,11bR)-9,11-bis(benzyloxy)-3-(dibenzylamino)-2,3,6,7-tetrahydro-1H-pyrido[2,1-a]isoquinolin-4(11bH)-one

Guidance literature:: With acetic acid; trifluoroacetic acid; In dichloromethane; for 24h; optical yield given as %de; diastereoselective reaction; Reflux;
DOI:10.1016/j.tet.2011.06.023

Reference yield:

: 188662-05-7
<2-<3,5-bis(benzyloxy)phenyl>ethyl>amine

: 1327254-72-7
(3S,11bS)-9,11-bis(benzyloxy)-3-(dibenzylamino)-2,3,6,7-tetrahydro-1H-pyrido[2,1-a]isoquinolin-4(11bH)-one

: (3S,11bR)-9,11-bis(benzyloxy)-3-(dibenzylamino)-2,3,6,7-tetrahydro-1H-pyrido[2,1-a]isoquinolin-4(11bH)-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: diisobutylaluminium hydride / tetrahydrofuran; hexane / 0 - 20 °C / Inert atmosphere

1.2: 17 h / Reflux; Inert atmosphere

2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.67 h / -78 °C

2.2: 0.5 h / -78 - 5 °C

3.1: acetic acid; trifluoroacetic acid / dichloromethane / 24 h / Reflux

With oxalyl dichloride; diisobutylaluminium hydride; acetic acid; dimethyl sulfoxide; trifluoroacetic acid; In tetrahydrofuran; hexane; dichloromethane; 2.1: Swern oxidation / 2.2: Swern oxidation / 3.1: Pictet-Spengler cyclisation;
DOI:10.1016/j.tet.2011.06.023