(R)-((1S,2S,4S,5R)-5-{3-[(Z)-Benzylimino]-propyl}-1-aza-bicyclo[2.2.2]oct-2-yl)-quinolin-4-yl-methanol

Base Information

• Chemical Name: (R)-((1S,2S,4S,5R)-5-{3-[(Z)-Benzylimino]-propyl}-1-aza-bicyclo[2.2.2]oct-2-yl)-quinolin-4-yl-methanol
• CAS No.: 445433-08-9
• Molecular Formula: C₂₇H₃₁N₃O
• Molecular Weight: 413.563
• Mol file: 445433-08-9.mol

Synonyms:(R)-((1S,2S,4S,5R)-5-{3-[(Z)-Benzylimino]-propyl}-1-aza-bicyclo[2.2.2]oct-2-yl)-quinolin-4-yl-methanol

Chemical Property of (R)-((1S,2S,4S,5R)-5-{3-[(Z)-Benzylimino]-propyl}-1-aza-bicyclo[2.2.2]oct-2-yl)-quinolin-4-yl-methanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-((1S,2S,4S,5R)-5-{3-[(Z)-Benzylimino]-propyl}-1-aza-bicyclo[2.2.2]oct-2-yl)-quinolin-4-yl-methanol

There total 2 articles about (R)-((1S,2S,4S,5R)-5-{3-[(Z)-Benzylimino]-propyl}-1-aza-bicyclo[2.2.2]oct-2-yl)-quinolin-4-yl-methanol 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: 98.0%

benzylamine (100-46-9) + 10,11-dihydrocinchonidine-11-carbaldehyde (445433-05-6) → (R)-((1S,2S,4S,5R)-5-{3-[(Z)-Benzylimino]-propyl}-1-aza-bicyclo[2.2.2]oct-2-yl)-quinolin-4-yl-methanol (445433-08-9)

Guidance literature:

In toluene; for 3h; Heating;

DOI:10.1021/jo0255173

Reference yield:

Cinchonidin (485-71-2) → (R)-((1S,2S,4S,5R)-5-{3-[(Z)-Benzylimino]-propyl}-1-aza-bicyclo[2.2.2]oct-2-yl)-quinolin-4-yl-methanol (445433-08-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 87 percent / [(2,4-di-t-Bu-C₆H₃-O)2POCH₂]4C; H₂ / Rh(CO)2acac / toluene / 20 h / 90 °C / 15001.5 Torr

2: 98 percent / toluene / 3 h / Heating

With [(2,4-di-t-Bu-C₆H₃-O)2POCH₂]4C; hydrogen; acetylacetonatodicarbonylrhodium(l); In toluene;

DOI:10.1021/jo0255173

Reference yield: 83.0%

(R)-((1S,2S,4S,5R)-5-{3-[(Z)-Benzylimino]-propyl}-1-aza-bicyclo[2.2.2]oct-2-yl)-quinolin-4-yl-methanol (445433-08-9) → 11-N-benzylaminomethyl-10,11-dihydrocinchonidine

Guidance literature:

With sodium tetrahydroborate; In ethanol; at 20 ℃; for 3h;

DOI:10.1021/jo0255173

upstream raw materials:

benzylamine

10,11-dihydrocinchonidine-11-carbaldehyde

Cinchonidin