1417616-20-6

Basic information

• Product Name: (2S,3R)-3-(6-bromo-1-tosyl-1H-indol-3-yl)-2-isopropyl-4-nitrobutanal
• Synonyms: (2S,3R)-3-(6-bromo-1-tosyl-1H-indol-3-yl)-2-isopropyl-4-nitrobutanal
• CAS NO: 1417616-20-6
• Molecular Weight: 507.405
• Mol File: 1417616-20-6.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (2S,3R)-3-(6-bromo-1-tosyl-1H-indol-3-yl)-2-isopropyl-4-nitrobutanal(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3R)-3-(6-bromo-1-tosyl-1H-indol-3-yl)-2-isopropyl-4-nitrobutanal(1417616-20-6)
• EPA Substance Registry System: (2S,3R)-3-(6-bromo-1-tosyl-1H-indol-3-yl)-2-isopropyl-4-nitrobutanal(1417616-20-6)

Safety Data

• Hazardous Substances Data: 1417616-20-6(Hazardous Substances Data)

Upstream product

• 52415-29-9 6-bromo-1H-indole 
• 158991-81-2 6-bromo-N-(1-p-toluenesulphonyl)-indole-3-carboxaldehyde 
• 1417616-02-4 (E)-6-bromo-3-(2-nitrovinyl)-1-tosyl-1H-indole 
• 590-86-3 isovaleraldehyde 
• 17826-04-9 6-bromo-1H-indole-3-carbaldehyde 

Relevant articles and documents

Organocatalytic asymmetric Michael addition of aliphatic aldehydes to indolylnitroalkenes: Access to contiguous stereogenic tryptamine precursors

Because of the importance of the indole framework and the versatile transformation of nitro and formyl groups, the efficient synthesis of optically pure 2-alkyl-3-(1H-indol-3-yl)-4-nitrobutanals, one type of tryptamine precursors are of great interest for pharmaceutical and biological research. Herein, the Michael addition of aliphatic aldehydes to indolylnitroalkenes has been developed using (S)-diphenylprolinol trimethylsilyl ether as an organocatalyst, which provides the desired optically pure syn 2-alkyl-3-(1H-indol-3-yl)-4-nitrobutanal derivatives in up to 98% yield with up to >99:1 dr and >99% ee. To show the synthetic usefulness of this methodology, optically active 2-alkyl-4-nitro-3-(1-tosyl-1H-indol-3-yl)butan-1- ol and tryptamine derivatives are readily obtained by stepwise systematic transformations.