N-(9-Deoxy-epi-cinchonin-9-yl)picolinaMide

Base Information

• Chemical Name: N-(9-Deoxy-epi-cinchonin-9-yl)picolinaMide
• CAS No.: 1414851-55-0
• Molecular Formula: C25H26N4O
• Molecular Weight: 398.5
• Mol file: 1414851-55-0.mol

Synonyms:N-(9-Deoxy-epi-cinchonin-9-yl)picolinaMide;N-(9-Deoxy-epi-cinchonin-9-yl)picolinamide

Chemical Property of N-(9-Deoxy-epi-cinchonin-9-yl)picolinaMide

Chemical Property:

• PSA: 58.12000
• LogP: 4.32610

Purity/Quality:

98%,99%, ^*data from raw suppliers

N-(9-Deoxy-epi-cinchonin-9-yl)picolinamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of N-(9-Deoxy-epi-cinchonin-9-yl)picolinaMide

There total 3 articles about N-(9-Deoxy-epi-cinchonin-9-yl)picolinaMide 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: 63.0%

pyridine-2-carbonyl chloride (29745-44-6) + 9-amino-9-deoxyepicinchonine → N-picolynoyl-9-amino-9-deoxy-epi-cinchonine (1414851-55-0)

Guidance literature:

With triethylamine; In tetrahydrofuran; at 0 - 20 ℃; for 24h;

DOI:10.1016/j.tetlet.2015.08.086

Reference yield: 60.0%

2-Picolinic acid (98-98-6) + (8R,9R)-9-amino(9-deoxy)epicinchonin → N-(9-deoxy-epi-cinchonin-9-yl)picolinamide (1414851-55-0)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20 ℃; for 1h; Inert atmosphere;

DOI:10.1021/ja309963w

Reference yield:

C19H22N2O → N-picolynoyl-9-amino-9-deoxy-epi-cinchonine (1414851-55-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: triphenylphosphine / tetrahydrofuran / 0.17 h / 0 °C

1.2: 27 h / 20 - 60 °C

1.3: 18 h / 50 °C

2.1: triethylamine / tetrahydrofuran / 24 h / 0 - 20 °C

With triethylamine; triphenylphosphine; In tetrahydrofuran;

DOI:10.1016/j.tetlet.2015.08.086

upstream raw materials:

2-Picolinic acid

pyridine-2-carbonyl chloride

Refernces

• 1、 Hayashi, Masashi,Shiomi, Noriyuki,Funahashi, Yasuhiro,Nakamura, Shuichi. "Cinchona alkaloid amides/dialkylzinc catalyzed enantioselective desymmetrization of aziridines with phosphites". supporting information. p. 19366 - 19369. Retrieved 2013/02/23.