1609247-46-2

Upstream product

• 54605-72-0 1-phenyl-1H-pyrazole-4-carbaldehyde 
• 106-95-6 allyl bromide 

Downstream Products

• 1609247-59-7 (4S,6R)-6-(bromomethyl)-4-(1-phenyl-1H-pyrazol-4-yl)-1,3-oxazinan-2-one 
• 1609247-60-0 (4S,6S)-6-(bromomethyl)-4-(1-phenyl-1H-pyrazol-4-yl)-1,3-oxazinan-2-one 
• 1609247-51-9 (S)-tert-butyl N-[1-(1-phenyl-1H-pyrazol-4-yl)-3-butenyl]carbamate 

Relevant academic research and scientific papers

Diastereoselective in and Zn-mediated allylation of pyrazol-4-yl derived (R)-tert-butanesulfinyl imines: Synthesis of enantiomerically pure 6-(pyrazol-4-yl)-piperidin-2,4-diones

The In and Zn-mediated allylation of substituted pyrazol-4-yl derived (R)-N-tert-butanesulfinyl imines proceeds with high diastereoselectivity depending on the conditions and additives (up to 99.4% de). Thus, the synthesized diastereomeric homoallylsulfinamides were isolated and characterized as pure diastereomers, which were then converted into the corresponding pyrazol-4-yl-derived N-Boc-homoallylamines via consecutive treatment with HCl and Boc2O. The latter were then subjected to a sequence of reactions: cyclobromocarbamation with NBS and enolate-isocyanate rearrangement with tBuOK to give novel enantiomerically pure (S)-6-(pyrazol-4-yl)-piperidine-2,4-diones in 88-96% yield. The absolute configurations of the allylation products were assigned by X-ray single crystal analysis of the intermediate bromomethylurethanes.