ethyl 3-hydroxy-3,6-dihydropyridine-1(2H)-carboxylate

Base Information

• Chemical Name: ethyl 3-hydroxy-3,6-dihydropyridine-1(2H)-carboxylate
• CAS No.: 66643-49-0
• Molecular Formula: C8H13NO3
• Molecular Weight: 171.19400
• DSSTox Substance ID: DTXSID20516118
• Nikkaji Number: J1.689.698E
• Mol file: 66643-49-0.mol

Synonyms:66643-49-0;ethyl 3-hydroxy-3,6-dihydropyridine-1(2H)-carboxylate;ethyl 3-hydroxy-3,6-dihydro-2H-pyridine-1-carboxylate;Ethyl 5-hydroxy-5,6-dihydropyridine-1(2H)-carboxylate;DTXSID20516118;HDWVZWCHYNYDFC-UHFFFAOYSA-N;AKOS017258907;SB54133;VS-12909;Ethyl5-hydroxy-5,6-dihydropyridine-1(2H)-carboxylate;ethyl 3-hydroxy-1,2,3,6-tetrahydropyridine-1-carboxylate;(+/-)-ethyl 5-hydroxy-5,6-dihydropyridine-1(2H)-carboxylate

Chemical Property of ethyl 3-hydroxy-3,6-dihydropyridine-1(2H)-carboxylate

Chemical Property:

• Boiling Point: 280.7±40.0 °C(Predicted)
• PKA: 14.17±0.20(Predicted)
• PSA: 49.77000
• Density: 1.206±0.06 g/cm3(Predicted)
• LogP: 0.31350
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 171.08954328
• Heavy Atom Count: 12
• Complexity: 191

Purity/Quality:

99% ^*data from raw suppliers

Ethyl5-hydroxy-5,6-dihydropyridine-1(2H)-carboxylate 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)N1CC=CC(C1)O

Technology Process of ethyl 3-hydroxy-3,6-dihydropyridine-1(2H)-carboxylate

There total 7 articles about ethyl 3-hydroxy-3,6-dihydropyridine-1(2H)-carboxylate 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:

ethyl 3-acetoxy-1,2,3,6-tetrahydropiperidine-1-carboxylate (66643-48-9) → ethyl 3-hydroxy-1,2,3,6-tetrahydropiperidine-1-carboxylate (66643-49-0)

Guidance literature:

With sodium hydroxide; In ethanol; at 0 ℃; for 1h; Yield given;

Reference yield:

pyridine (110-86-1) → ethyl 3-hydroxy-1,2,3,6-tetrahydropiperidine-1-carboxylate (66643-49-0)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 49 h / 20 - 140 °C

1.2: 12 h / 20 °C

2.1: toluene / 2.5 h / Reflux

3.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 18 h / 20 °C

4.1: hydrogen bromide / chloroform / 3.5 h / -50 °C

5.1: pyridine / 18 h / 20 °C

6.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / 2 h / 90 °C

7.1: sodium hydroxide / ethanol / 1.5 h / 0 °C

With pyridine; hydrogen bromide; 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-chloro-benzenecarboperoxoic acid; sodium hydroxide; In ethanol; chloroform; toluene;

DOI:10.1039/c7cc02699d

Reference yield:

1-benzyl-1,2,3,6-tetrahydropyridine (40240-12-8) → ethyl 3-hydroxy-1,2,3,6-tetrahydropiperidine-1-carboxylate (66643-49-0)

Guidance literature:

Multi-step reaction with 6 steps

1: toluene / 2.5 h / Reflux

2: 3-chloro-benzenecarboperoxoic acid / chloroform / 18 h / 20 °C

3: hydrogen bromide / chloroform / 3.5 h / -50 °C

4: pyridine / 18 h / 20 °C

5: 1,8-diazabicyclo[5.4.0]undec-7-ene / 2 h / 90 °C

6: sodium hydroxide / ethanol / 1.5 h / 0 °C

With pyridine; hydrogen bromide; 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-chloro-benzenecarboperoxoic acid; sodium hydroxide; In ethanol; chloroform; toluene;

DOI:10.1039/c7cc02699d

upstream raw materials:

ethyl 3-acetoxy-1,2,3,6-tetrahydropiperidine-1-carboxylate

pyridine

1-benzyl-1,2,3,6-tetrahydropyridine

ethyl 1,2,3,6-tetrahydropyridine-1-carboxylate

Downstream raw materials:

1-ethoxycarbonyl-1,2,3,6-tetrahydro-3-pyridyl diphenylphosphinate

6-Hydroxy-7-oxo-2-aza-bicyclo[2.2.2]octane-2-carboxylic acid benzyl ester

6,6-Dimethoxy-7-oxo-2-aza-bicyclo[2.2.2]octane-2-carboxylic acid benzyl ester

7-Hydroxy-6,6-dimethoxy-2-aza-bicyclo[2.2.2]octane-2-carboxylic acid benzyl ester