Benzyl 4-methylidenepyrazolidine-1-carboxylate

Base Information

• Chemical Name: Benzyl 4-methylidenepyrazolidine-1-carboxylate
• CAS No.: 503072-31-9
• Molecular Formula: C12H14N2O2
• Molecular Weight: 218.255
• DSSTox Substance ID: DTXSID50514223
• Wikidata: Q82374417
• Mol file: 503072-31-9.mol

Synonyms:Benzyl 4-methylidenepyrazolidine-1-carboxylate;503072-31-9;SCHEMBL4854985;4-methylene-pyrazolidine-1-carboxylic acid 1-benzyl ester;DTXSID50514223;ZXPWSWRNPBDBGH-UHFFFAOYSA-N

Chemical Property of Benzyl 4-methylidenepyrazolidine-1-carboxylate

Chemical Property:

• XLogP3: 1.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 218.105527694
• Heavy Atom Count: 16
• Complexity: 272

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C=C1CNN(C1)C(=O)OCC2=CC=CC=C2

Technology Process of Benzyl 4-methylidenepyrazolidine-1-carboxylate

There total 3 articles about Benzyl 4-methylidenepyrazolidine-1-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: 98.0%

4-methylenepyrazolidine-1,2-dicarboxylic acid 1-benzyl ester 2-tert-butyl ester (503072-28-4) → 4-methylene-pyrazolidine-1-carboxylic acid 1-benzyl ester (503072-31-9)

Guidance literature:

With thionyl chloride; In methanol;

DOI:10.1016/j.bmcl.2004.06.001

Reference yield:

2-chloromethyl-3-chloroprop-1-ene (1871-57-4) + 1-tert-butoxycarbonyl-2-carbobenzyloxyhydrazine (57699-88-4) → 4-methylene-pyrazolidine-1-carboxylic acid 1-benzyl ester (503072-31-9)

Guidance literature:

With NaH; In N,N-dimethyl-formamide;

Reference yield:

N-benzyloxycarbonyl-hydrazine (5331-43-1) → 4-methylene-pyrazolidine-1-carboxylic acid 1-benzyl ester (503072-31-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 99 percent / Et₃N / CH₂Cl₂

2: 96 percent / NaH / dimethylformamide

3: 98 percent / SOCl₂ / methanol

With thionyl chloride; sodium hydride; triethylamine; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2004.06.001

upstream raw materials:

4-methylenepyrazolidine-1,2-dicarboxylic acid 1-benzyl ester 2-tert-butyl ester

N-benzyloxycarbonyl-hydrazine

2-chloromethyl-3-chloroprop-1-ene

1-tert-butoxycarbonyl-2-carbobenzyloxyhydrazine

Downstream raw materials:

2-[2-(4-fluorophenyl)acetyl]-4-methylene-pyrazolidine-1-carboxylic acid benzyl ester

8-[2-(4-Fluoro-phenyl)-acetyl]-1,4-dioxa-7,8-diaza-spiro[4.4]nonane-7-carboxylic acid benzyl ester

2-[2-(4-fluorophenyl)acetyl]-4-oxo-pyrazolidine-1-carboxylic acid benzyl ester