883566-22-1

Basic information

• Product Name: 4-isopropyl-4-phenyl-1-triisopropylsilyl-1,4-dihydropyridine
• CAS NO: 883566-22-1
• Molecular Weight: 355.639
• Mol File: 883566-22-1.mol

Chemical Properties

• CAS DataBase Reference: 4-isopropyl-4-phenyl-1-triisopropylsilyl-1,4-dihydropyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 4-isopropyl-4-phenyl-1-triisopropylsilyl-1,4-dihydropyridine(883566-22-1)
• EPA Substance Registry System: 4-isopropyl-4-phenyl-1-triisopropylsilyl-1,4-dihydropyridine(883566-22-1)

Safety Data

• Hazardous Substances Data: 883566-22-1(Hazardous Substances Data)

Upstream product

• 939-23-1 p-phenylpyridine 
• 80522-42-5 triisopropylsilyl trifluoromethanesulfonate 
• 3536-97-8 diisopropylmagnesium 

Downstream Products

• 553631-47-3 4-isopropyl-4-phenylpiperidine 

Relevant articles and documents

Direct synthesis of 4,4-disubstituted N-silyl-1,4-dihydropyridines

An unprecedented method for the preparation of 4,4-disubstituted 1,4-dihydropyridines is presented. It is based on the trapping reaction of 4-substitued N-silylpyridinium ions. When performed with dialkylmagnesium reagents, such as iPr2Mg, silyl protected 4,4-disubstituted 1,4-dihydropyridines were obtained in up to quantitative yields. High 1,4-selectivity was found for sterically demanding nucleophiles, whereas small nucleophiles (Me2Mg) tend to yield 1,2-addition-products. Grignard, dialkylzinc and organocopper reagents were found to give either no addition products or less favorable results. Reduction of the obtained 1,4-dihydropyridine with NaCNBH3 in the presence of HCl, followed by treatment with tert-butyl dicarbonate provided the corresponding N-Boc protected piperidines with high yields.