(S)-tert-butyl 2-vinylpyrrolidine-1-carboxylate

Base Information

• Chemical Name: (S)-tert-butyl 2-vinylpyrrolidine-1-carboxylate
• CAS No.: 115393-77-6
• Molecular Formula: C11H19NO2
• Molecular Weight: 197.277
• DSSTox Substance ID: DTXSID00454645
• Nikkaji Number: J1.070.184H
• Wikidata: Q82276293
• Mol file: 115393-77-6.mol

Synonyms:115393-77-6;(S)-tert-butyl 2-vinylpyrrolidine-1-carboxylate;Tert-butyl (2S)-2-ethenylpyrrolidine-1-carboxylate;tert-butyl (2S)-2-vinylpyrrolidine-1-carboxylate;(2S)-N-tert-butoxycarbonyl-2-vinylpyrrolidine;1-Pyrrolidinecarboxylic acid, 2-ethenyl-, 1,1-dimethylethyl ester, (2S)-;SCHEMBL5848791;(2S)-1-Boc-2-vinylpyrrolidine;DTXSID00454645;HYHWHEBWKXKPGG-SECBINFHSA-N;PS-18227;CS-0168099;P19226;Tert-butyl (S)-2-vinylpyrrolidine-1-carboxylate;tert-butyl(2S)-2-vinylpyrrolidine-1-carboxylate;(2S)-1-(tert-Butoxycarbonyl)-2-vinylpyrrolidine;A854123;J-502538

Chemical Property of (S)-tert-butyl 2-vinylpyrrolidine-1-carboxylate

Chemical Property:

• Boiling Point: 248.4±29.0 °C(Predicted)
• PKA: -1.99±0.40(Predicted)
• PSA: 29.54000
• Density: 1.050±0.06 g/cm3(Predicted)
• LogP: 2.50980
• 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

(S)-tert-Butyl2-vinylpyrrolidine-1-carboxylate 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1CCCC1C=C
• Isomeric SMILES: CC(C)(C)OC(=O)N1CCC[C@H]1C=C

Technology Process of (S)-tert-butyl 2-vinylpyrrolidine-1-carboxylate

There total 29 articles about (S)-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: 97.0%

Boc-L-Pro-H (69610-41-9,117625-90-8) + methyl-triphenylphosphonium iodide (2065-66-9) → tert-butyl (S)-2-vinylpyrrolidine-1-carboxylate (115393-77-6)

Guidance literature:

methyl-triphenylphosphonium iodide; With potassium tert-butylate; In diethyl ether; at 20 ℃; for 2h; Inert atmosphere;

Boc-L-Pro-H; In diethyl ether; Inert atmosphere;

DOI:10.1021/acs.joc.6b02562

Reference yield: 94.0%

(E)-6-((tert-butoxycarbonyl)amino)hex-2-en-1-ol (1008751-38-9) → tert-butyl (S)-2-vinylpyrrolidine-1-carboxylate (115393-77-6)

Guidance literature:

With cyclopentadienylruthenium(II) trisacetonitrile hexafluorophosphate; allyl (R)-6-(2-chloronaphthalen-1-yl)-5-methylpyridine-2-carboxylate; In N,N-dimethyl acetamide; at 100 ℃; for 3h; optical yield given as %ee; enantioselective reaction; Inert atmosphere;

DOI:10.1021/ol203218d

Reference yield: 89.5%

ammonium chloride + Boc-L-Pro-H (69610-41-9,117625-90-8) + Methyltriphenylphosphonium bromide (1779-49-3) → tert-butyl (S)-2-vinylpyrrolidine-1-carboxylate (115393-77-6)

Guidance literature:

With n-butyllithium; In diethyl ether; hexane; ethyl acetate;

upstream raw materials:

N-(tert-butoxycarbonyl)-L-prolinol

Methyltriphenylphosphonium bromide

Boc-L-Pro-H

Methylenetriphenylphosphorane

Downstream raw materials:

(S)-1-(o-iodobenzoyl)-2-vinylpyrrolidine

(S)-1-(o-iodobenzoyl)-2-vinylpyrrolidine

tert-butyl (2R)-2-ethylpyrrolidine-1-carboxylate

(S)-7-(benzyloxymethyl)-2,3-dihydro-1H-pyrrolizin-5(7aH)-one