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

Base Information

• Chemical Name: (-)-(3S,11bS)-3-(tert-butoxycarbonylamino)-9,11-bis(benzyloxy)-2,3,6,7-tetrahydro-1H-pyrido[2,1-a]isoquinolin-4(11bH)-one
• CAS No.: 949463-59-6
• Molecular Formula: C₃₂H₃₆N₂O₅
• Molecular Weight: 528.648
• Mol file: 949463-59-6.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 13 articles about (-)-(3S,11bS)-3-(tert-butoxycarbonylamino)-9,11-bis(benzyloxy)-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: 92.0%

(-)-(3S,11bS)-3-(tert-butoxycarbonylamino)-9,11-dihydroxy-2,3,6,7-tetrahydro-1H-pyrido[2,1-a]isoquinolin-4(11bH)-one (949463-73-4) + benzyl bromide (100-39-0) → (-)-(3S,11bS)-3-(tert-butoxycarbonylamino)-9,11-bis(benzyloxy)-2,3,6,7-tetrahydro-1H-pyrido[2,1-a]isoquinolin-4(11bH)-one (949463-59-6)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; caesium carbonate; In N,N-dimethyl-formamide; at 0 ℃; for 1h;

DOI:10.1021/jo070560h

Reference yield: 82.3%

tert-butyl (3S)-9,11-dihydroxy-4-oxo-2,3,4,6,7,11b-hexahydro-1H-pyrido[2,1-a]isoquinolin-3-ylcarbamate + benzyl bromide (100-39-0) → (-)-(3S,11bS)-3-(tert-butoxycarbonylamino)-9,11-bis(benzyloxy)-2,3,6,7-tetrahydro-1H-pyrido[2,1-a]isoquinolin-4(11bH)-one (949463-59-6) + (+)-(3S,11bR)-3-(tert-butoxycarbonylamino)-9,11-bis(benzyloxy)-2,3,6,7-tetrahydro-1H-pyrido[2,1-a]isoquinolin-4(11bH)-one (949463-60-9)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 12h;

DOI:10.1016/j.tet.2011.06.023

Reference yield: 57.0%

di-tert-butyl dicarbonate (24424-99-5) + (3S)-3-amino-9,11-bis(benzyloxy)-2,3,6,7-tetrahydro-1H-pyrido[2,1-a]isoquinolin-4(11bH)-one → (-)-(3S,11bS)-3-(tert-butoxycarbonylamino)-9,11-bis(benzyloxy)-2,3,6,7-tetrahydro-1H-pyrido[2,1-a]isoquinolin-4(11bH)-one (949463-59-6) + (+)-(3S,11bR)-3-(tert-butoxycarbonylamino)-9,11-bis(benzyloxy)-2,3,6,7-tetrahydro-1H-pyrido[2,1-a]isoquinolin-4(11bH)-one (949463-60-9)

Guidance literature:

In dichloromethane; at 20 ℃; for 24h;

upstream raw materials:

(-)-(3S,11bS)-3-(tert-butoxycarbonylamino)-9,11-dihydroxy-2,3,6,7-tetrahydro-1H-pyrido[2,1-a]isoquinolin-4(11bH)-one

benzyl bromide

methyl (S)-2-(benzyloxycarbonylamino)-5-(3,5-bis(benzyloxy)phenethylamino)-5-oxopentanoate

benzyl (3S,11bS)-9,11-bis(benzyloxy)-4-oxo-2,3,4,6,7,11b-hexahydro-1H-pyrido[2,1-a]isoquinolin-3-ylcarbamate

Downstream raw materials:

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

(S)-N-((3S,11bS)-9,11-bis(benzyloxy)-4-oxo-2,3,4,6,7,11b-hexahydro-1H-pyrido[2,1-a]isoquinolin-3-yl)-16-((4S,5S)-5-decyl-2,2-dimethyl-1,3-dioxolan-4-yl)-14-(methoxymethoxy)hexadecanamide

(14S,17S,18S)-N-((3S,11bS)-9,11-bis(benzyloxy)-4-oxo-2,3,4,6,7,11b-hexahydro-1H-pyrido[2,1-a]isoquinolin-3-yl)-14,17,18-trihydroxyoctacosanamide

tert-butyl (3R,11bS)-9,11-bis(benzyloxy)-2,3,4,6,7,11b-hexahydro-4-oxo-1H-pyrido[2,1-a]isoquinolin-3-ylcarbamate