Tert-butyl 3-methylenepyrrolidine-1-carboxylate

Base Information

• Chemical Name: Tert-butyl 3-methylenepyrrolidine-1-carboxylate
• CAS No.: 114214-71-0
• Molecular Formula: C10H17NO2
• Molecular Weight: 183.25
• Hs Code.: 2933990090
• European Community (EC) Number: 852-476-1
• DSSTox Substance ID: DTXSID20571121
• Wikidata: Q72490498
• Mol file: 114214-71-0.mol

Synonyms:114214-71-0;tert-butyl 3-methylenepyrrolidine-1-carboxylate;tert-butyl 3-methylidenepyrrolidine-1-carboxylate;1-Boc-3-methylenepyrrolidine;1-Pyrrolidinecarboxylic acid, 3-methylene-, 1,1-dimethylethyl ester;3-Methylenepyrrolidine-1-carboxylic Acid tert-Butyl Ester;MFCD12407903;1-BOC-3-METHYLENE-PYRROLIDINE;3-Methylene-pyrrolidine-1-carboxylic acid tert-butyl ester;tert-Butyl3-methylenepyrrolidine-1-carboxylate;SCHEMBL1063509;SCHEMBL8253350;DTXSID20571121;PXTONRTYYUAUJU-UHFFFAOYSA-N;AKOS015841217;PB15089;1-t-butoxycarbonyl-3-methylenepyrrolidine;AM802951;AS-42461;SY097967;CS-0048277;EN300-266664;A803151;J-524560;3-Methylene pyrrolidine-1-carboxylic acid tert-butyl ester

Chemical Property of Tert-butyl 3-methylenepyrrolidine-1-carboxylate

Chemical Property:

• Boiling Point: 236.7±29.0 °C(Predicted)
• PKA: -1.49±0.20(Predicted)
• PSA: 29.54000
• Density: 1.01±0.1 g/cm3(Predicted)
• LogP: 2.12130
• Storage Temp.: 2-8°C
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 183.125928785
• Heavy Atom Count: 13
• Complexity: 228

Purity/Quality:

97% ^*data from raw suppliers

3-Methylenepyrrolidine-1-carboxylicAcidtert-ButylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1CCC(=C)C1
• Uses: 3-Methylenepyrrolidine-1-carboxylic Acid tert-Butyl Ester, can be used as an intermediate for variety of chemical synthesis. It can be used for the preparation of aminomethylated 4-fluoropiperidines and 3-fluoropyrrolidines, which are of specific interest as bifunctional building blocks for fluorinated pharmaceutical compds.

Technology Process of Tert-butyl 3-methylenepyrrolidine-1-carboxylate

There total 5 articles about Tert-butyl 3-methylenepyrrolidine-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: 83.0%

→ tert-butyl 3-methylidenepyrrolidine-1-carboxylate (114214-71-0)

Guidance literature:

With potassium tert-butylate; In diethyl ether; for 1h; Inert atmosphere; Reflux;

In diethyl ether; at 20 ℃; for 0.5h; Inert atmosphere;

Reference yield: 70.0%

Methyltriphenylphosphonium bromide (1779-49-3) + 3-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester (101385-93-7) → tert-butyl 3-methylidenepyrrolidine-1-carboxylate (114214-71-0)

Guidance literature:

With potassium tert-butylate; In diethyl ether;

DOI:10.1039/c8cc07432a

Reference yield: 61.0%

methyl-triphenylphosphonium iodide (2065-66-9) + 3-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester (101385-93-7) → tert-butyl 3-methylidenepyrrolidine-1-carboxylate (114214-71-0)

Guidance literature:

methyl-triphenylphosphonium iodide; With sodium hydride; In tetrahydrofuran; at 5 - 10 ℃; for 1h; Inert atmosphere;

3-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester; In tetrahydrofuran; at 5 - 20 ℃; for 12h; Inert atmosphere;

upstream raw materials:

3-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester

tert-butyl 3-[(4-methylphenyl)sulfonyloxymethyl]pyrrolidine-1-carboxylate

methyl-triphenylphosphonium iodide

Methyltriphenylphosphonium bromide

Downstream raw materials:

3-bromomethyl-1-tert-butoxycarbonyl-3-fluoropyrrolidine

6-azaspiro[3.4]octane-6-carboxylic acid,2-oxo-,1,1-dimethylethyl ester

2-hydroxy-7-azaspiro[3.4]octane-7-carboxylic acid tert-butyl ester

C₁₉H₂₇NO₅S