1173199-96-6

Basic information

• Product Name: (R)-tert-butyl 2-[(R)-1-hydroxy-3-phenylpropyl]-5,6-dihydropyridine-1(2H)-carboxylate
• Synonyms: (R)-tert-butyl 2-[(R)-1-hydroxy-3-phenylpropyl]-5,6-dihydropyridine-1(2H)-carboxylate
• CAS NO: 1173199-96-6
• Molecular Weight: 317.428
• Mol File: 1173199-96-6.mol

Chemical Properties

• CAS DataBase Reference: (R)-tert-butyl 2-[(R)-1-hydroxy-3-phenylpropyl]-5,6-dihydropyridine-1(2H)-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-tert-butyl 2-[(R)-1-hydroxy-3-phenylpropyl]-5,6-dihydropyridine-1(2H)-carboxylate(1173199-96-6)
• EPA Substance Registry System: (R)-tert-butyl 2-[(R)-1-hydroxy-3-phenylpropyl]-5,6-dihydropyridine-1(2H)-carboxylate(1173199-96-6)

Safety Data

• Hazardous Substances Data: 1173199-96-6(Hazardous Substances Data)

Upstream product

• 104-53-0 3-phenyl-propionaldehyde 
• 1386393-97-0 tert-butyl 4-[(1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonyl)oxy]-3,6-dihydropyridine-1(2H)-carboxylate 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 79099-07-3 N-tert-butyloxycarbonylpiperidin-4-one 
• 138647-49-1 4-Trifluoromethanesulfonyloxy-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester 

Relevant articles and documents

Optimization and multigram scalability of a catalytic enantioselective borylative migration for the synthesis of functionalized chiral piperidines

The development of new, efficient and economical methods for the preparation of functionalized, optically enriched piperidines is important in the field of drug discovery where this class of heterocycles is often deemed a privileged structure. We have optimized a Pd-catalyzed enantioselective borylative migration of an alkenyl nonaflate derivative of the simple precursor, N-Boc-4-piperidone. This anomalous borylation reaction lends access to a chiral optically enriched piperidinyl allylic boronate that can be employed in carbonyl allylboration and stereoselective cross-coupling to produce substituted dehydropiperidines related to numerous pharmaceutical agents. A systematic fine-tuning of reaction conditions revealed that diethyl ether and the green solvent cyclopentyl methyl ether are suitable reaction solvents providing the highest enantioselectivity (up to 92% ee) under a low catalyst loading of 3 mol%. Optimization of the aldehyde allylboration step led to higher yields with further solvent economy. The multigram-scalability of the entire process was demonstrated under the reaction conditions that provide optimal atom-economy and efficiency.

α-Hydroxyalkyl heterocycles via chiral allylic boronates: Pd-catalyzed borylation leading to a formal enantioselective isomerization of allylic ether and amine

(Chemical Equation Presented) An efficient catalytic enantioselective preparation of synthetically useful pyranyl and piperidinyl allylic boronates was achieved via a palladium-catalyzed borylation/isomerization reaction on the corresponding alkenyl triflates. The influence of the base and solvent was found to be crucial on the regio- and enantioselectivity of this reaction. The overall borylation process constitutes a successful example of formal asymmetric isomerization of allylic ether/amine. The resulting allylic boronate reagents add to various aldehydes in a one-pot process to give synthetically useful alpha-hydroxyalkyl derivatives in high stereoselectivity.