188660-19-7

Upstream product

• 501-53-1 benzyl chloroformate 
• 110-86-1 pyridine 
• 79328-85-1 N-benzyloxycarbonyl-1,2-dihydropyridine 
• 188660-16-4 (S)-N-Carbobenzoxy-3-hydroxy-1,2,3,4-tetrahydropyridine 
• 179748-56-2 (+/-)-N-Carbobenzoxy-3-hydroxy-1,2,3,4-tetrahydropyridine 
• 109-00-2 3-HYDROXYPYRIDINE 
• 188660-17-5 (R)-3-Acetoxy-3,4-dihydro-2H-pyridine-1-carboxylic acid benzyl ester 

Downstream Products

• 278593-54-7 N-Benzoxy-3-bromo-5-hydroxy-2-methoxypiperidine 
• 100858-34-2 benzyl (3R)-3-hydroxypiperidine-1-carboxylate 
• 329771-35-9 (S)-3-((Z)-3-Methoxy-allyl)-3,6-dihydro-2H-pyridine-1-carboxylic acid benzyl ester 
• 329771-34-8 3-(2-oxo-ethyl)-3,6-dihydro-2H-pyridine-1-carboxylic acid benzyl ester 
• 174956-48-0 benzyl (3R)-3-hydroxy-3,6-dihydropyridine-1(2H)-carboxylate 

Relevant academic research and scientific papers

Enantioselective Synthesis of Chiral Piperidines via the Stepwise Dearomatization/Borylation of Pyridines

We have developed a novel approach for the synthesis of enantioenriched 3-boryl-tetrahydropyridines via the Cu(I)-catalyzed regio-, diastereo-, and enantioselective protoborylation of 1,2-dihydropyridines, which were obtained by the partial reduction of the pyridine derivatives. This dearomatization/enantioselective borylation stepwise strategy provides facile access to chiral piperidines together with the stereospecific transformation of a stereogenic C-B bond from readily available starting materials. Furthermore, the utility of this method is demonstrated for the concise synthesis of the antidepressant drug (-)-paroxetine. A theoretical study of the reaction mechanism is also described.

Lipase-mediated synthesis of enantiopure N-carbobenzoxy-3-hydroxy- 1,2,3,4-tetrahydro- and N-carbobenzoxy-3-hydroxy-1,2,3,6-tetrahydropyridines from 3-hydroxypyridine

Two isomeric chiral hydroxytetrahydropyridines, having high potential utility for the construction of a variety of chiral amine derivatives, have been prepared in both enantiomeric forms by employing lipase-mediated resolution starting from 3-hydroxypyridine. Thus, on exposure to sodium borohydride in the presence of carbobenzoxy chloride, 3-hydroxypyridine has been found to furnish racemic N-carbobenzoxy-3-hydroxy-1,2,3,4- tetrahydropyridine, which is resolved under trans-esterification conditions in the presence of lipase PS to give both enantiomeric products in enantiopure forms. Isomerization of the chiral 1,2,3,4-tetrahydro-product into the chiral 1,2,3,6-tetrahydro-derivative has been accomplished without loss of the original chiral integrity. The racemic 1,2,3,6-tetrahydro- derivative has also been resolved under the same lipase-mediated trans- esterification conditions.

A Facile Synthesis of (R)-4-Amino-3-hydroxybutanoic Acid (GABOB) from 3-Hydroxypyridine

(R)-4-Amino-3-hydroxybutanoic acid (GABOB) has been synthesized facilely from 3-hydroxypyridine via 1-carbobenzoxy-1,2,3,4-tetrahydro-3-hydroxypyridine employing lipase-mediated kinetic resolution.