trans-3'-Hydroxy Cotinine Benzoate

Base Information

• Chemical Name: trans-3'-Hydroxy Cotinine Benzoate
• CAS No.: 146275-16-3
• Molecular Formula: C17H16N2O3
• Molecular Weight: 296.326
• Mol file: 146275-16-3.mol

Synonyms:trans-3'-Hydroxy Cotinine Benzoate;(3R-trans)-3-(Benzoyloxy)-1-Methyl-5-(3-pyridinyl)-2-pyrrolidinone

Chemical Property of trans-3'-Hydroxy Cotinine Benzoate

Chemical Property:

• PSA: 59.50000
• LogP: 2.14830
• Solubility.: Dichloromethane, Methanol

Purity/Quality:

98% ^*data from raw suppliers

trans-3''-HydroxyCotinineBenzoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Cotinine derivative. Carcinogen.

Technology Process of trans-3'-Hydroxy Cotinine Benzoate

There total 7 articles about trans-3'-Hydroxy Cotinine Benzoate 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:

3-pyridinecarboxaldehyde (500-22-1) → (3R,5S)-1-methyl-3-benzoyloxy-5-(3-pyridyl)pyrrolidin-2-one (146275-16-3)

Guidance literature:

Multi-step reaction with 7 steps

1: 94 percent / toluene / 20 h / Heating

2: 80 percent / CH₂Cl₂ / 168 h / Heating

3: 76 percent / aq. HCl / ethanol / 5 h / 20 °C

4: H₂O / 2 h / 20 °C

5: 9.3 mg / Et₃SiH; CF₃CO₂H / CH₂Cl₂ / 0.5 h / Heating

6: 54 percent / H₂ / Pd/C / aq. ethanol / 1.5 h

7: DEAD; PPh₃ / toluene / 0.08 h / 20 °C

With hydrogenchloride; triethylsilane; hydrogen; triphenylphosphine; trifluoroacetic acid; diethylazodicarboxylate; palladium on activated charcoal; In ethanol; dichloromethane; water; toluene; 7: Mitsunobu reaction;

DOI:10.1016/j.tet.2004.08.023

Reference yield:

(Z)-(3-pyridyl)-N-(2',3':5',6'-O-diisopropylidene-α-L-gulofuranosyl)methylideneamine N-oxide → (3R,5S)-1-methyl-3-benzoyloxy-5-(3-pyridyl)pyrrolidin-2-one (146275-16-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 80 percent / CH₂Cl₂ / 168 h / Heating

2: 76 percent / aq. HCl / ethanol / 5 h / 20 °C

3: H₂O / 2 h / 20 °C

4: 9.3 mg / Et₃SiH; CF₃CO₂H / CH₂Cl₂ / 0.5 h / Heating

5: 54 percent / H₂ / Pd/C / aq. ethanol / 1.5 h

6: DEAD; PPh₃ / toluene / 0.08 h / 20 °C

With hydrogenchloride; triethylsilane; hydrogen; triphenylphosphine; trifluoroacetic acid; diethylazodicarboxylate; palladium on activated charcoal; In ethanol; dichloromethane; water; toluene; 6: Mitsunobu reaction;

DOI:10.1016/j.tet.2004.08.023

Reference yield:

(2S)-N-[[(3S,5S)-3-(3-pyridyl)isoxazolidin-5-yl]carbonyl]bornane-10,2-sultam (796843-63-5) → (3R,5S)-1-methyl-3-benzoyloxy-5-(3-pyridyl)pyrrolidin-2-one (146275-16-3)

Guidance literature:

Multi-step reaction with 4 steps

1: H₂O / 2 h / 20 °C

2: 9.3 mg / Et₃SiH; CF₃CO₂H / CH₂Cl₂ / 0.5 h / Heating

3: 54 percent / H₂ / Pd/C / aq. ethanol / 1.5 h

4: DEAD; PPh₃ / toluene / 0.08 h / 20 °C

With triethylsilane; hydrogen; triphenylphosphine; trifluoroacetic acid; diethylazodicarboxylate; palladium on activated charcoal; In ethanol; dichloromethane; water; toluene; 4: Mitsunobu reaction;

DOI:10.1016/j.tet.2004.08.023

upstream raw materials:

benzoic acid

cis-(3'S,5'S)-3'-hydroxycotinine

3-pyridinecarboxaldehyde

(2S)-N-[[(3S,5S)-3-(3-pyridyl)isoxazolidin-5-yl]carbonyl]bornane-10,2-sultam

Downstream raw materials:

trans-3'-Hydroxycotinine

Refernces