(S)-tert-Butyl 2-(tributylstannyl)pyrrolidine-1-carboxylate

Base Information

Chemical Name:(S)-tert-Butyl 2-(tributylstannyl)pyrrolidine-1-carboxylate
CAS No.:123387-67-7
Molecular Formula:C₂₁H₄₃NO₂Sn
Molecular Weight:460.288
Hs Code.:
Mol file:123387-67-7.mol

Synonyms:1-Pyrrolidinecarboxylicacid,2-(tributylstannyl)-,1,1-dimethylethyl ester,(2S)-;137496-74-3;AKOS015911247;(S)-tert-Butyl 2-(tributylstannyl)pyrrolidine-1-carboxylate

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (S)-tert-Butyl 2-(tributylstannyl)pyrrolidine-1-carboxylate

Chemical Property:

Hydrogen Bond Donor Count:0
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:12
Exact Mass:461.231582
Heavy Atom Count:25
Complexity:370

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:

Useful:

Canonical SMILES:CCCC[Sn](CCCC)(CCCC)C1CCCN1C(=O)OC(C)(C)C
Isomeric SMILES:CCCC[Sn](CCCC)(CCCC)[C@H]1CCCN1C(=O)OC(C)(C)C

Technology Process of (S)-tert-Butyl 2-(tributylstannyl)pyrrolidine-1-carboxylate

There total 1 articles about (S)-tert-Butyl 2-(tributylstannyl)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: 70.0%

: 20763-88-6
tributylstannyl radical

: 86953-79-9
tert-butyl pyrrolidine-1-carboxylate

: 137496-74-3,123387-67-7
(S)-N-(tert-butoxycarbonyl)-2-(tributylstannyl)pyrrolidine

Guidance literature:: With sec.-butyllithium; (-)-sparteine; In diethyl ether; sec-BuLi was added to soln. of sparteine and pyrrolidine at -78°C; reaction time 4-6 h; addn. of tin-compound soln.; warming to room temperature (3 h);; flash chromatography with ethyl acetate/hexane; (1)H-and (13)C-NMR; elem. anal.;
DOI:10.1021/ja00025a066

Reference yield: 81.0%

: 137496-74-3,123387-67-7
(S)-N-(tert-butoxycarbonyl)-2-(tributylstannyl)pyrrolidine

: 626-62-0
Cyclohexyl iodide

: 1448219-19-9
tert-butyl (R)-2-cyclohexylpyrrolidine-1-carboxylate

Guidance literature:: (S)-N-(tert-butoxycarbonyl)-2-(tributylstannyl)pyrrolidine; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 2h; Inert atmosphere;

With zinc(II) iodide; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 0.666667h; Cooling with acetone-dry ice; Schlenk technique; Inert atmosphere;

Cyclohexyl iodide; With (1,2-dimethoxyethane)dichloronickel(II); (1R,2R)-N,N’-dimethyl-1,2-di(naphthalen-1-yl)ethane-1,2-diamine; In tetrahydrofuran; hexane; at 20 ℃; for 60h; enantioselective reaction; Inert atmosphere;
DOI:10.1021/ja4054114

Reference yield:

: 137496-74-3,123387-67-7
(S)-N-(tert-butoxycarbonyl)-2-(tributylstannyl)pyrrolidine

: 626-62-0
Cyclohexyl iodide

: 1448219-19-9
tert-butyl (R)-2-cyclohexylpyrrolidine-1-carboxylate

: 1448219-27-9
tert-butyl (S)-2-cyclohexylpyrrolidine-1-carboxylate

Guidance literature:: (S)-N-(tert-butoxycarbonyl)-2-(tributylstannyl)pyrrolidine; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 2h; Inert atmosphere;

With zinc(II) iodide; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 0.666667h; Cooling with acetone-dry ice; Schlenk technique; Inert atmosphere;

Cyclohexyl iodide; With (1,2-dimethoxyethane)dichloronickel(II); (1S,2S)-N,N’-dimethyl-1,2-di(naphthalen-1-yl)ethane-1,2-diamine; In tetrahydrofuran; hexane; at 20 ℃; for 60h; Overall yield = 83 %; Overall yield = 105 mg; enantioselective reaction; Inert atmosphere;
DOI:10.1021/ja4054114