Tert-butyl 2-vinylpyrrolidine-1-carboxylate

Base Information

• Chemical Name: Tert-butyl 2-vinylpyrrolidine-1-carboxylate
• CAS No.: 176324-60-0
• Molecular Formula: C11H19NO2
• Molecular Weight: 197.277
• European Community (EC) Number: 809-968-6
• DSSTox Substance ID: DTXSID70552228
• Mol file: 176324-60-0.mol

Synonyms:176324-60-0;tert-butyl 2-vinylpyrrolidine-1-carboxylate;N-Boc-2-Vinylpyrrolidine;tert-Butyl 2-ethenylpyrrolidine-1-carboxylate;1-Boc-2-Vinylpyrrolidine;vinyl N-boc-pyrrolidine;SCHEMBL3563098;(S)-1-Boc-2-vinylpyrrolidine;DTXSID70552228;HYHWHEBWKXKPGG-UHFFFAOYSA-N;BHA32460;MFCD12923195;MFCD22381778;AKOS026715650;SY318667;WS-00793;tert-butyl2-vinylpyrrolidine-1-carboxylate;CS-0079636;EN300-1223746;A905609;2-Vinylpyrrolidine-1-carboxylic acid tert-butyl ester;2-Vinyl-pyrrolidine-1-carboxylic acid tert-butyl ester;F2147-2046

Chemical Property of Tert-butyl 2-vinylpyrrolidine-1-carboxylate

Chemical Property:

• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 197.141578849
• Heavy Atom Count: 14
• Complexity: 230

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1CCCC1C=C

Technology Process of Tert-butyl 2-vinylpyrrolidine-1-carboxylate

There total 8 articles about Tert-butyl 2-vinylpyrrolidine-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: 96.0%

5-hexenylazide (821-77-2) + di-tert-butyl dicarbonate (24424-99-5) → 2-(R)-Vinyl-pyrrolidine-1-carboxylic Acid Tert-Butyl Ester (176324-60-0)

Guidance literature:

With C₂₂H₃₀Cl₂FeN₂O; In benzene; at 100 ℃; Inert atmosphere;

DOI:10.1021/jacs.7b00270

Reference yield: 89.0%

N-(tert-butoxycarbonyl)pyrrolidine-2-carboxaldehyde (59378-82-4,117625-90-8) + Methyltriphenylphosphonium bromide (1779-49-3) → 2-(R)-Vinyl-pyrrolidine-1-carboxylic Acid Tert-Butyl Ester (176324-60-0)

Guidance literature:

Methyltriphenylphosphonium bromide; With potassium tert-butylate; In diethyl ether; for 1h; Heating;

N-(tert-butoxycarbonyl)pyrrolidine-2-carboxaldehyde; In diethyl ether; at 20 ℃;

DOI:10.1016/j.tet.2005.01.048

Reference yield: 76.0%

tert-butyl 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrrolidine-1-carboxylate + tetravinyltin (IV) (1112-56-7) → 2-(R)-Vinyl-pyrrolidine-1-carboxylic Acid Tert-Butyl Ester (176324-60-0)

Guidance literature:

tetravinyltin (IV); With n-butyllithium; In hexane; at 20 ℃; for 0.5h; Inert atmosphere;

tert-butyl 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrrolidine-1-carboxylate; In tetrahydrofuran; diethyl ether; at -78 - -42 ℃; for 0.833333h; Further stages;

DOI:10.1002/anie.201611273

upstream raw materials:

N-(tert-butoxycarbonyl)pyrrolidine-2-carboxaldehyde

Methyltriphenylphosphonium bromide

Boc-L-Pro-H

5-hexenylazide

Downstream raw materials:

2-(2-oxoethyl)pyrrolidine-1-carboxylic acid tert-butyl ester

2-vinylpyrrolidine hydrochloride

1-(N-benzylamino)-2-vinylpyrrolidine

2-vinylpyrrolidine