nornicotine

Base Information

• Chemical Name: nornicotine
• CAS No.: 13450-58-3
• Molecular Weight: 148.20498
• Mol file: 13450-58-3.mol

Synonyms:3-((2S)PYRROLIDIN-2-YL)PYRIDINE hydrochloride

Chemical Property of nornicotine

Chemical Property:

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of nornicotine

There total 131 articles about nornicotine 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: 85.0%

(S)-3-(1-azido-but-3-enyl)pyridine (314280-29-0) → nornicotine (494-97-3,13450-58-3)

Guidance literature:

With bis(cyclohexanyl)borane; In tetrahydrofuran; at -15 - 20 ℃; for 12h;

DOI:10.1021/jo010386b

Reference yield: 72.0%

(S)-3-(1,4-dichlorobutyl)pyridine → nornicotine (494-97-3,13450-58-3)

Guidance literature:

With ammonium hydroxide; potassium carbonate; at 60 ℃; for 5h; Reagent/catalyst;

Reference yield: 69.0%

(S)-5-bromonornicotine (R)-(+)-α-methoxy-α-trifluoromethylphenyl acetic acid salt → nornicotine (494-97-3,13450-58-3)

Guidance literature:

(S)-5-bromonornicotine (R)-(+)-α-methoxy-α-trifluoromethylphenyl acetic acid salt; With potassium hydroxide; In water; for 1h;

With palladium 10% on activated carbon; hydrogen; triethylamine; In ethanol; at 20 ℃;

DOI:10.1021/acscombsci.6b00179

upstream raw materials:

Myosmine

5-(pyridin-3-yl)pyrrolidin-2-one

3-(1-Hydroxy-2-pyrrolidinyl)pyridine

2,2,5,5-tetrametyl-1-aza-2,5-disilacyclopentane-1-propyl magnesium bromide

Downstream raw materials:

N-acetylnornicotine

N'-ethyl-S-nornicotine

3-((S)-1-allyl-pyrrolidin-2-yl)-pyridine

N'-Nitrosonornicotine

Refernces

• 1、 Del Castillo, Estefanía,Mu?iz, Kilian. "Enantioselective Synthesis of Nicotine via an Iodine-Mediated Hofmann-L?ffler Reaction". . p. 705 - 708. Retrieved 2019.
• 2、 Tsai, Mui-Chiung,Sai, Yang,Li, Yan,Aislaitner, George,Gorrod, John W.. "The biosynthesis of [5'-14C]cotinine and other radiolabeled nicotine metabolites". . p. 387 - 407. Retrieved 1999.
• 3、 Uchida,Maeda,Kisaki. "Conversion of nicotine into nornicotine and N-methylmyosmine by fungi". . p. 1949 - 1953. Retrieved 1983.
• 4、 Hao Dong-yun,Yeoman. "Mechanism of nicotine N-demethylation in tobacco cell suspension cultures". . p. 477 - 482. Retrieved 1996.
• 5、 Jacob III. "Resolution of (±)-5-bromonornicotine. Synthesis of (R)- and (S)-nornicotine of high enantiomeric purity". . p. 4165 - 4167. Retrieved 1982.
• 6、 Seeman, Jeffrey I.,Chavdarian, Charles G.,Secor, Henry V.. "Synthesis of the Enantiomers of Nornicotine". . p. 5419 - 5421. Retrieved 1985.
• 7、 Ahles, Sebastian,Beeck, Sebastian,Wegner, Hermann A.. "Orthogonal Catalysis for an Enantioselective Domino Inverse-Electron Demand Diels?Alder/Substitution Reaction". supporting information. . Retrieved 2021/12/09.
• 8、 -. "Method for synthesizing chiral nicotine from butyrolactone". . . Retrieved 2021/11/03.