(2S,5S)-tert-butyl 2-((tert-butyldiphenylsilyloxy)methyl)-5-cyanopyrrolidine-1-carboxylate

Base Information

• Chemical Name: (2S,5S)-tert-butyl 2-((tert-butyldiphenylsilyloxy)methyl)-5-cyanopyrrolidine-1-carboxylate
• CAS No.: 192389-31-4
• Molecular Formula: C₂₇H₃₆N₂O₃Si
• Molecular Weight: 464.68
• Mol file: 192389-31-4.mol

Synonyms:(2S,5S)-tert-butyl 2-((tert-butyldiphenylsilyloxy)methyl)-5-cyanopyrrolidine-1-carboxylate

Chemical Property of (2S,5S)-tert-butyl 2-((tert-butyldiphenylsilyloxy)methyl)-5-cyanopyrrolidine-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,5S)-tert-butyl 2-((tert-butyldiphenylsilyloxy)methyl)-5-cyanopyrrolidine-1-carboxylate

There total 2 articles about (2S,5S)-tert-butyl 2-((tert-butyldiphenylsilyloxy)methyl)-5-cyanopyrrolidine-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: 72.0%

trimethylsilyl cyanide (7677-24-9) + (2S,5S/R)-N-tert-butoxycarbonyl-2-(tert-butyldiphenylsilyloxy)methyl-5-methoxy-pyrrolidine (192389-29-0) → (2S,5R)-tert-butyl 2-((tert-butyldiphenylsilyloxy)methyl)-5-cyanopyrrolidine-1-carboxylate (192389-30-3) + (2S,5S)-tert-butyl 2-((tert-butyldiphenylsilyloxy)methyl)-5-cyanopyrrolidine-1-carboxylate (192389-31-4)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -35 ℃; for 0.05h;

DOI:10.1002/chem.200400181

Reference yield:

(S)-2-((tert-butyldiphenylsilyloxy)methyl)-1-chloropyrrolidine (948992-89-0) + diethyl cyanophosphonate (2942-58-7) + di-tert-butyl dicarbonate (24424-99-5) → (2S,5R)-tert-butyl 2-((tert-butyldiphenylsilyloxy)methyl)-5-cyanopyrrolidine-1-carboxylate (192389-30-3) + (2S,5S)-tert-butyl 2-((tert-butyldiphenylsilyloxy)methyl)-5-cyanopyrrolidine-1-carboxylate (192389-31-4)

Guidance literature:

(S)-2-((tert-butyldiphenylsilyloxy)methyl)-1-chloropyrrolidine; With 2,2,6,6-tetramethylpiperidinyl-lithium; In tetrahydrofuran; hexane; at -78 ℃;

diethyl cyanophosphonate; With 1H-imidazole; In tetrahydrofuran; at 20 ℃; for 1.5h;

di-tert-butyl dicarbonate; With sodium hydroxide; In tetrahydrofuran; at 20 ℃; Further stages.;

DOI:10.1016/j.bmc.2007.05.064

Reference yield: 58.0%

(2S,5S)-tert-butyl 2-((tert-butyldiphenylsilyloxy)methyl)-5-cyanopyrrolidine-1-carboxylate (192389-31-4) → (2S,5R)-tert-butyl 5-aminomethyl-2-((tert-butyldiphenylsilyloxy)methyl)-5-cyanopyrrolidine-1-carboxylate

Guidance literature:

With ammonia; hydrogen; nickel; In ethanol; for 20h; under 3750.38 Torr;

DOI:10.1016/j.bmc.2007.05.064

upstream raw materials:

trimethylsilyl cyanide

(2S,5S/R)-N-tert-butoxycarbonyl-2-(tert-butyldiphenylsilyloxy)methyl-5-methoxy-pyrrolidine

(S)-2-((tert-butyldiphenylsilyloxy)methyl)-1-chloropyrrolidine

diethyl cyanophosphonate

Downstream raw materials:

(2S,5R)-tert-butyl 2-((tert-butyldiphenylsilyloxy)methyl)-5-cyanopyrrolidine-1-carboxylate

(2S,5S,2'S,5'S,2''S,5''S)-N'-(4'''-nitrophenyl)sulfonyl-2,5''-bis-(hydroxymethyl)-dodecahydro-terpyrrole

(2S,5S,2'S,5'S,2''S,5''S)-N,N''-di-tert-butoxycarbonyl-N'-(4'''-nitrophenyl)sulfonyl-2,5''-bis-[hydroxymethyl]-dodecahydro-terpyrrole

(2S,5S,2'S,5'S,2''S,5''S)-2,5''-bis-[(tert-butyldiphenylsilyloxy)methyl]-dodecahydro-terpyrrole