(S)-1-BOC-2-TRIBUTYLSTANNANYLPYRROLIDINE

Base Information

• Chemical Name: (S)-1-BOC-2-TRIBUTYLSTANNANYLPYRROLIDINE
• CAS No.: 137496-74-3
• Molecular Formula: C₂₁H₄₃NO₂Sn
• Molecular Weight: 460.288
• Hs Code.: 2933990090
• Mol file: 137496-74-3.mol

Synonyms:1-Pyrrolidinecarboxylicacid, 2-(tributylstannyl)-, 1,1-dimethylethyl ester, (S)-;(S)-2-(Tributyltin)-N-(tert-butoxycarbonyl)pyrrolidine;(S)-N-tert-Butoxycarbonyl-2-(tributylstannyl)pyrrolidine

Chemical Property of (S)-1-BOC-2-TRIBUTYLSTANNANYLPYRROLIDINE

Chemical Property:

• PSA: 29.54000
• LogP: 7.13200

Purity/Quality:

99% ^*data from raw suppliers

(S)-1-BOC-2-TRIBUTYLSTANNANYLPYRROLIDINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (S)-1-BOC-2-TRIBUTYLSTANNANYLPYRROLIDINE

There total 1 articles about (S)-1-BOC-2-TRIBUTYLSTANNANYLPYRROLIDINE 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%

tributylstannyl radical (20763-88-6) + tert-butyl pyrrolidine-1-carboxylate (86953-79-9) → (S)-N-(tert-butoxycarbonyl)-2-(tributylstannyl)pyrrolidine (137496-74-3,123387-67-7)

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%

(S)-N-(tert-butoxycarbonyl)-2-(tributylstannyl)pyrrolidine (137496-74-3,123387-67-7) + Cyclohexyl iodide (626-62-0) → tert-butyl (R)-2-cyclohexylpyrrolidine-1-carboxylate (1448219-19-9)

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:

(S)-N-(tert-butoxycarbonyl)-2-(tributylstannyl)pyrrolidine (137496-74-3,123387-67-7) + Cyclohexyl iodide (626-62-0) → tert-butyl (R)-2-cyclohexylpyrrolidine-1-carboxylate (1448219-19-9) + tert-butyl (S)-2-cyclohexylpyrrolidine-1-carboxylate (1448219-27-9)

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

upstream raw materials:

tributylstannyl radical

tert-butyl pyrrolidine-1-carboxylate

Downstream raw materials:

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

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