1(2H)-Pyridinecarboxylic acid, 2-[[[(1,1-dimethylethyl)diphenylsilyl]oxy]methyl]-3,4-dihydro-6-[[(trifluoro methyl)sulfonyl]oxy]-, methyl ester, (2S)-

Base Information

• Chemical Name: 1(2H)-Pyridinecarboxylic acid, 2-[[[(1,1-dimethylethyl)diphenylsilyl]oxy]methyl]-3,4-dihydro-6-[[(trifluoro methyl)sulfonyl]oxy]-, methyl ester, (2S)-
• CAS No.: 442202-21-3
• Molecular Formula: C25H30F3NO6SSi
• Molecular Weight: 557.663
• Mol file: 442202-21-3.mol

Synonyms:

Chemical Property of 1(2H)-Pyridinecarboxylic acid, 2-[[[(1,1-dimethylethyl)diphenylsilyl]oxy]methyl]-3,4-dihydro-6-[[(trifluoro methyl)sulfonyl]oxy]-, methyl ester, (2S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1(2H)-Pyridinecarboxylic acid, 2-[[[(1,1-dimethylethyl)diphenylsilyl]oxy]methyl]-3,4-dihydro-6-[[(trifluoro methyl)sulfonyl]oxy]-, methyl ester, (2S)-

There total 2 articles about 1(2H)-Pyridinecarboxylic acid, 2-[[[(1,1-dimethylethyl)diphenylsilyl]oxy]methyl]-3,4-dihydro-6-[[(trifluoro methyl)sulfonyl]oxy]-, methyl ester, (2S)- 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: 96.0%

N-(5-chloropyridin-2-yl)-1,1,1-trifluoro-N-[(trifluoromethyl)sulphonyl]methanesulphonamide (145100-51-2) + methyl (6S)-(-)-2-(tert-butyldiphenylsilyloxymethyl)-6-oxopiperidine-1-carboxylate (442202-20-2) → methyl (6S)-(-)-2-(tert-butyldiphenylsilyloxymethyl)-6-trifluoromethanesulfonyloxy-3,4-dihydro-2H-pyridine-1-carboxylate (442202-21-3)

Guidance literature:

methyl (6S)-(-)-2-(tert-butyldiphenylsilyloxymethyl)-6-oxopiperidine-1-carboxylate; With n-butyllithium; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h;

N-(5-chloropyridin-2-yl)-1,1,1-trifluoro-N-[(trifluoromethyl)sulphonyl]methanesulphonamide; In tetrahydrofuran; hexane; at -78 - -40 ℃; for 1h;

DOI:10.1016/j.tet.2004.05.039

Reference yield:

(S)-6-((tert-butyldiphenylsilyloxy)methyl)piperidin-2-one (209257-75-0) → methyl (6S)-(-)-2-(tert-butyldiphenylsilyloxymethyl)-6-trifluoromethanesulfonyloxy-3,4-dihydro-2H-pyridine-1-carboxylate (442202-21-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

1.2: 98 percent / tetrahydrofuran; hexane / 2 h / -78 - 0 °C

2.1: hexamethyldisilazane; n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

2.2: 96 percent / tetrahydrofuran; hexane / 1 h / -78 - -40 °C

With n-butyllithium; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; hexane;

DOI:10.1016/j.tet.2004.05.039

Reference yield: 91.0%

Benzyl propargyl ether (4039-82-1) + methyl (6S)-(-)-2-(tert-butyldiphenylsilyloxymethyl)-6-trifluoromethanesulfonyloxy-3,4-dihydro-2H-pyridine-1-carboxylate (442202-21-3) → methyl (2S)-(-)-6-(3-benzyloxyprop-1-ynyl)-2-tert-butyldiphenylsilyloxymethyl-3,4-dihydro-2H-pyridine-1-carboxylate (880881-66-3)

Guidance literature:

With diisopropylamine; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; at 20 ℃; for 20h;

DOI:10.3987/COM-05-S(K)7

upstream raw materials:

N-(5-chloropyridin-2-yl)-1,1,1-trifluoro-N-[(trifluoromethyl)sulphonyl]methanesulphonamide

methyl (6S)-(-)-2-(tert-butyldiphenylsilyloxymethyl)-6-oxopiperidine-1-carboxylate

(S)-6-((tert-butyldiphenylsilyloxy)methyl)piperidin-2-one

Downstream raw materials:

dimethyl (S)-(-)-6-(tert-butyldiphenylsilyloxymethyl)-5,6-dihydro-4H-pyridine-1,2-dicarboxylate

methyl (2S)-(-)-6-(3-benzyloxyprop-1-ynyl)-2-tert-butyldiphenylsilyloxymethyl-3,4-dihydro-2H-pyridine-1-carboxylate

methyl (2S,6S)-2-(3-benzyloxyprop-1-ynyl)-6-propenylpiperidine-1-carboxylate

methyl (2S,6S)-(-)-2-(3-benzyloxyprop-1-ynyl)-6-hydroxymethylpiperidine-1-carboxylate