156782-68-2

Basic information

• Product Name: Benzyl 4-(4-fluorophenyl)-4-hydroxypiperidine-1-carboxylate
• Synonyms: Benzyl 4-(4-fluorophenyl)-4-hydroxypiperidine-1-carboxylate
• CAS NO: 156782-68-2
• Molecular Formula: C19H20FNO3
• Molecular Weight: 329.371
• Mol File: 156782-68-2.mol

Chemical Properties

• CAS DataBase Reference: Benzyl 4-(4-fluorophenyl)-4-hydroxypiperidine-1-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: Benzyl 4-(4-fluorophenyl)-4-hydroxypiperidine-1-carboxylate(156782-68-2)
• EPA Substance Registry System: Benzyl 4-(4-fluorophenyl)-4-hydroxypiperidine-1-carboxylate(156782-68-2)

Safety Data

• Hazardous Substances Data: 156782-68-2(Hazardous Substances Data)

Upstream product

• 19099-93-5 benzyl 4-oxo-1-piperidinecarboxylate 
• 460-00-4 1-Bromo-4-fluorobenzene 
• 501-53-1 benzyl chloroformate 
• 95798-23-5 1-(benzyloxycarbonyl)-4-hydroxypiperidine 
• 5382-16-1 4-HYDROXYPIPERIDINE 
• 130387-74-5 4-fluorophenylmagnesium chloride 

Downstream Products

• 400770-92-5 benzyl 4-(4-fluorophenyl)-3,6-dihydropyridine-1(2H)-carboxylate 
• 871926-97-5 4-(4-fluoro-phenyl)-3,4-dihydroxy-piperidine-1-carboxylic acid benzyl ester 

Relevant articles and documents

Catalytic Friedel-Crafts Reactions on Saturated Heterocycles and Small Rings for sp3-sp2 Coupling of Medicinally Relevant Fragments

gem-Diarylheterocycles display a wide range of biological activity. Here we present a systematic study into the formation of 4- to 6-membered O- and N-heterocycles and cyclobutanes bearing the diaryl motif through a catalytic Friedel–Crafts reaction from the corresponding benzylic alcohols. 3,3-Diaryltetrahydrofurans, 4,4-diaryltetrahydropyrans, 3,3-diarylpyrrolidines, 4,4-diaryl-piperidines, as well as diarylcyclobutanes are examined, with results for 3,3-diaryloxetanes and 3,3-diarylazetidines presented for comparison. Three catalytic systems are investigated for each substrate [Ca(II), Li(I) and Fe(III)], across preinstalled aromatic groups of differing electronic character. In most cases examined, the diaryl product is obtained directly from the alcohol with good yields using the most appropriate catalyst system. In the absence of a nucleophile, the olefins from the 5- and 6-membered substrates by elimination of water are obtained under the same reaction conditions.

Synthesis of (±)-coerulescine and a formal synthesis of (±)-horsfiline

A straightforward synthesis of (±)-coerulescine and (±)-horsfiline has been established from 3-formyl-3-phenylpyrrolidine employing 4-hydroxypiperidine as the starting material. There are two remarkable steps for the synthesis of (±)-coerulescine and (±)-horsfiline. One is the rapid access to produce 3-formyl-3-phenylpyrrolidine by Lewis acid-catalyzed rearrangement of 3,4-dihydroxy-4-phenylpiperidine. The other key step is an intramolecular electrophilic cyclization from 3-benzylcarbamoyl-3- phenylpyrrolidine to the 3,3-spirocyclic 2-oxindole ring skeleton.