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

Base Information

• Chemical Name: (S)-tert-butyl 2-ethynylpyrrolidine-1-carboxylate
• CAS No.: 130495-08-8
• Molecular Formula: C₁₁H₁₇NO₂
• Molecular Weight: 195.261
• European Community (EC) Number: 863-614-5
• DSSTox Substance ID: DTXSID00452560
• Nikkaji Number: J1.387.301A
• Wikidata: Q72503155
• Mol file: 130495-08-8.mol

Synonyms:130495-08-8;(S)-tert-butyl 2-ethynylpyrrolidine-1-carboxylate;(S)-1-Boc-2-Ethynylpyrrolidine;tert-butyl (2S)-2-ethynylpyrrolidine-1-carboxylate;(S)-N-BOC-2-ETHYNYLPYRROLIDINE;tert-butyl (S)-2-ethynylpyrrolidine-1-carboxylate;1-Pyrrolidinecarboxylic acid, 2-ethynyl-, 1,1-dimethylethyl ester, (2S)-;(S)-N-tert-Butoxycarbonyl-2-ethynylpyrrolidine;SCHEMBL231219;DTXSID00452560;1-BOC-2-(S)-ethynylpyrrolidine;MKFYNQAKTJFISL-SECBINFHSA-N;(S)-N-Boc-2-Ethynyl-pyrrolidine;(2S)-1-Boc-2-ethynylpyrrolidine;CS-B1739;MFCD10698161;AKOS025294281;AS-36517;AM20080216;1-t-butyloxycarbonyl-2-(s)-ethynylpyrrolidine;EN300-298780;(S)-tert-butyl2-ethynylpyrrolidine-1-carboxylate;(S)-N-(tert-butoxycarbonyl)-2-ethynylpyrrolidine;A888736;tert-butyl(2s)-2-ethynylpyrrolidine-1-carboxylate;(2S)-N-(tert-Butoxycarbonyl)-2-ethynylpyrrolidine;J-524444;(2S)-1-(tert-Butoxycarbonyl)-2alpha-ethynylpyrrolidine;(S)-2-Ethynyl-pyrrolidine-1-carboxylic acid tert-butyl ester;1-Pyrrolidinecarboxylic acid,2-ethynyl-,tert-butyl ester,(2S)-

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

Chemical Property:

• Vapor Pressure: 0.023mmHg at 25°C
• Boiling Point: 249.165oC at 760 mmHg
• Flash Point: 104.491oC
• PSA: 29.54000
• Density: 1.041g/cm3
• LogP: 1.95700
• Storage Temp.: 2-8°C
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 195.125928785
• Heavy Atom Count: 14
• Complexity: 269

Purity/Quality:

98%min ^*data from raw suppliers

(s)-tert-butyl2-ethynylpyrrolidine-1-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

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-ethynylpyrrolidine-1-carboxylate

There total 19 articles about (S)-tert-butyl 2-ethynylpyrrolidine-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: 100.0%

Boc-L-Pro-H (69610-41-9,117625-90-8) + dimethyl diazomethylphosphonate (27491-70-9,28447-24-7,25411-73-8) → (S)-tert-butyl 2-ethynylpyrrolidine-1-carboxylate (130418-90-5,130495-08-8)

Guidance literature:

With potassium carbonate; In methanol; at 20 ℃; for 18h; Inert atmosphere;

DOI:10.1002/cmdc.201900618

Reference yield: 91.0%

(S)-2-(2,2-dibromoethenyl)-1-pyrrolidinecarboxylic acid 1,1-dimethylethyl ester (130419-38-4) → (S)-tert-butyl 2-ethynylpyrrolidine-1-carboxylate (130418-90-5,130495-08-8)

Guidance literature:

With sec.-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 1h; Inert atmosphere;

DOI:10.1002/adsc.201000678

Reference yield: 83.0%

dimethyl 1-(1-diazo-2-oxopropyl)phosphonate (90965-06-3) + tert-butyl (2S)-2-{[N-methoxy(N-methyl)amino]carbonyl}pyrrolidine-1-carboxylate (115186-37-3) → (S)-tert-butyl 2-ethynylpyrrolidine-1-carboxylate (130418-90-5,130495-08-8)

Guidance literature:

tert-butyl (2S)-2-{[N-methoxy(N-methyl)amino]carbonyl}pyrrolidine-1-carboxylate; With diisobutylaluminium hydride; In n-heptane; dichloromethane; at -78 ℃;

dimethyl 1-(1-diazo-2-oxopropyl)phosphonate; With potassium carbonate; In methanol; n-heptane; dichloromethane; at 20 ℃; Further stages.;

DOI:10.1016/j.tetlet.2004.05.139

upstream raw materials:

Boc-L-Pro-H

(S)-2-(2,2-dibromoethenyl)-1-pyrrolidinecarboxylic acid 1,1-dimethylethyl ester

n-butyllithium

diazomethyl-trimethyl-silane

Downstream raw materials:

(S)-tert-butyl-2-((4-((3-chloro-4-((3-fluorobenzyl)oxy)phenyl)amino)thieno[3,2-d]pyrimidin-6-yl)ethynyl)pyrrolidine-1-carboxylate

(S)-2-(1-phenyl-1H-1,2,3-triazol-4-yl)pyrrolidine-1-carboxylic acid tert-butyl ester

(S)-2-(5-((R)-1-phenylethylcarbamoyl)-1H-1,2,3-triazol-4-yl)pyrrolidine-1-carboxylic acid tert-butyl ester

(S)-2-(5-((S)-1-phenylethylcarbamoyl)-1H-1,2,3-triazol-4-yl)pyrrolidine-1-carboxylic acid tert-butyl ester

Refernces

• 1、 Bolli, Martin H.,Boss, Christoph,Brotschi, Christine,Gatfield, John,Heidmann, Bibia,Jenck, Francois,Roch, Catherine,Sifferlen, Thierry,Treiber, Alexander,Williams, Jodi T.. "From Oxadiazole to Triazole Analogues: Optimization toward a Dual Orexin Receptor Antagonist with Improved in vivo Efficacy in Dogs". . . Retrieved 2020/01/25.
• 2、 Shi, Ge,Wang, Sheng,Guan, Xiaoyan,Zhang, Jie,Wan, Xinhua. "Synthesis and thermo-responsive behavior of helical polyacetylenes derived from proline". supporting information. p. 12081 - 12084. Retrieved 2018/11/21.