Tert-butyl 2-(trimethylsilyl)pyrrolidine-1-carboxylate

Base Information

• Chemical Name: Tert-butyl 2-(trimethylsilyl)pyrrolidine-1-carboxylate
• CAS No.: 123387-66-6
• Molecular Formula: C₁₂H₂₅NO₂Si
• Molecular Weight: 243.421
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID50438617
• Nikkaji Number: J1.310.990G
• Mol file: 123387-66-6.mol

Synonyms:123387-66-6;tert-butyl 2-(trimethylsilyl)pyrrolidine-1-carboxylate;Tert-butyl 2-trimethylsilylpyrrolidine-1-carboxylate;tert-Butyl 2-(trimethylsilyl)-pyrrolidine-1-carboxylate;1-Pyrrolidinecarboxylic acid, 2-(trimethylsilyl)-, 1,1-dimethylethyl ester;tert-Butyl2-(trimethylsilyl)pyrrolidine-1-carboxylate;SCHEMBL16032626;DTXSID50438617;HJGAXMDEXCEYGL-UHFFFAOYSA-N;AKOS015910916;2-(Trimethylsilyl)-1-pyrrolidinecarboxylic acid tert-butyl ester;1-Pyrrolidinecarboxylicacid,2-(trimethylsilyl)-,1,1-dimethylethyl ester

Chemical Property of Tert-butyl 2-(trimethylsilyl)pyrrolidine-1-carboxylate

Chemical Property:

• Boiling Point: 279.9±33.0 °C(Predicted)
• PKA: -0.56±0.40(Predicted)
• PSA: 29.54000
• Density: 0.95±0.1 g/cm3(Predicted)
• LogP: 3.62110
• Storage Temp.: 2-8°C
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 243.165455575
• Heavy Atom Count: 16
• Complexity: 265

Purity/Quality:

99%min ^*data from raw suppliers

tert-Butyl 2-(trimethylsilyl)-pyrrolidine-1-carboxylate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1CCCC1[Si](C)(C)C

Technology Process of Tert-butyl 2-(trimethylsilyl)pyrrolidine-1-carboxylate

There total 16 articles about Tert-butyl 2-(trimethylsilyl)pyrrolidine-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: 95.0%

chloro-trimethyl-silane (75-77-4) + tert-butyl pyrrolidine-1-carboxylate (86953-79-9) → N-tert-butoxycarbonyl-2-trimethylsilylpyrrolidine (137496-67-4,142131-95-1,145416-70-2,123387-66-6)

Guidance literature:

With N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium; In diethyl ether; at -78 ℃; for 3h;

DOI:10.1016/0040-4039(94)85336-3

Reference yield: 94.0%

chloro-trimethyl-silane (75-77-4) + (±)-tert-butyl-2-phenylpyrrolidine-1-carboxylate (154874-88-1) → N-tert-butoxycarbonyl-2-trimethylsilylpyrrolidine (137496-67-4,142131-95-1,145416-70-2,123387-66-6)

Guidance literature:

With N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium; In tetrahydrofuran; at -78 ℃; for 0.5h;

DOI:10.1021/jo970985b

Reference yield: 87.0%

chloro-trimethyl-silane (75-77-4) + tert-butyl pyrrolidine-1-carboxylate (86953-79-9) → (S)-N-tert-butyloxycarbonyl-2-trimethylsilylpyrrolidine (123387-66-6,142131-95-1,145416-70-2,137496-67-4)

Guidance literature:

tert-butyl pyrrolidine-1-carboxylate; With sec.-butyllithium; (-)-sparteine; In diethyl ether; cyclohexane; at -78 ℃; for 3h; Inert atmosphere;

chloro-trimethyl-silane; In diethyl ether; cyclohexane; at -78 - 20 ℃; for 16h; optical yield given as %ee; enantioselective reaction; Inert atmosphere;

DOI:10.1002/adsc.201101016

upstream raw materials:

chloro-trimethyl-silane

tert-butyl pyrrolidine-1-carboxylate

(±)-tert-butyl-2-phenylpyrrolidine-1-carboxylate

N-(tert-butyloxycarbonyl) azide

Downstream raw materials:

2,5-bis(trimethylsilyl)-N-benzylpyrrolidine

Refernces

• 1、 McGrath, Matthew J.,Bilke, Julia L.,O'Brien, Peter. "Reactivity series for s-BuLi/diamine-mediated lithiation of N-Boc pyrrolidine: Applications in catalysis and lithiation of N-Boc piperidine". . p. 2607 - 2609. Retrieved 2006.
• 2、 Dong, Jing-Chao,Wang, Xin,Li, Run-Tao,Zhang, Hong-Mei,Cheng, Tie-Ming,Li, Chang-Ling. "Synthesis and analgesic activity of hydrochlorides and quaternary ammoniums of epibatidine incorporated with amino acid ester". . p. 4327 - 4329. Retrieved 2003.
• 3、 Dearden, Michael J.,Firkin, Catherine R.,Hermet, Jean-Paul R.,O'Brien, Peter. "A readily-accessible (+)-sparteine surrogate". . p. 11870 - 11871. Retrieved 2002.
• 4、 Pandey, Ganesh,Bagul, Trusar D.,Lakshmaiah, G.. "An Expeditious Synthesis of Epibatidine and Analogues". . p. 7439 - 7442. Retrieved 1994.
• 5、 Gallagher, Donald J.,Wu, Shengde,Nikolic, Nikola A.,Beak, Peter. "Chiral Organolithium Complexes: The Effect of Ligand Structure on the Enantioselective Deprotonation of Boc-Pyrrolidine". . p. 8148 - 8154. Retrieved 1995.
• 6、 Phuan, Puay-Wah,Ianni, James C.,Kozlowski, Marisa C.. "Is the A-ring of sparteine essential for high enantioselectivity in the asymmetric lithiation-substitution of N-Boc-pyrrolidine?". . p. 15473 - 15479. Retrieved 2004.
• 7、 Foley, Vera M.,Cano, Rafael,McGlacken, Gerard P.. "The search for an easily-prepared sparteine surrogate". . p. 1160 - 1167. Retrieved 2016/11/04.
• 8、 Praz, Jezabel,Guenee, Laure,Aziz, Sarwar,Berkessel, Albrecht,Alexakis, Alexandre. "Evaluation of the chiral DIANANE backbone as ligand for organolithium reagents". supporting information; experimental part. p. 1780 - 1790. Retrieved 2012/07/28.