3979-67-7

Upstream product

• 58657-81-1 1-benzyl-3-phenyl-piperidin-3-ol; hydrochloride 
• 1008-88-4 3-phenylpyridine 
• 100-39-0 benzyl bromide 
• 100-59-4 phenylmagnesium chloride 
• 40114-49-6 1-benzyl-3-piperidone 
• 58879-07-5 N-benzyl-3-hydroxy-3-phenylpiperidine 
• 100-58-3 phenylmagnesium bromide 
• 2959-96-8 2-phenylglutaric anhydride 
• 101999-42-2 (+/-)-2-phenyl-1,5-pentanediol 
• 100-46-9 benzylamine 

Downstream Products

• 3973-62-4 3-phenylpiperidine 
• 430461-56-6 (R)-3-phenyl piperidine 
• 1196713-21-9 (3S)-3-(4-aminophenyl)piperidine 
• 59349-71-2 (S)-3-phenylpiperidine hydrochloride 
• 1335523-82-4 4-(3S-piperidine-3-yl)bromobenzene 

Relevant academic research and scientific papers

A hydrogen borrowing annulation strategy for the stereocontrolled synthesis of saturated aza-heterocycles

An iridium catalyzed method for the synthesis of saturated aza-heterocycles from amines and diols is reported. A wide range of substituted heterocycles can be obtained using this approach including products bearing substituents at the C2, C3 and C4 positions. Employing water as the solvent, enantiopure diols could undergo annulation with minimal racemization, enabling the synthesis of valuable enantioenriched C3 and C4-substituted saturated aza-heterocycles.

Synthesis method for (R)-3-phenylpiperidine or/and (S)-3-phenylpiperidine and synthesis method for chiral intermediate of niraparib

The invention belongs to the technical field of organic synthesis. The synthesis method firstly provided by the invention takes benzyl-4-oxopiperidine as a starting material, and the starting materialis subjected to Grignard reaction, elimination reaction, hydrogenation reduction reaction and chiral resolution in sequence to successfully obtain a target product (R)-3-phenylpiperidine or/ and (S)-3-phenylpiperidine. The synthesis method sencondly provided by the invention takes the same starting raw material for Grignard reaction, organic silicon reagent is used for removing a hydroxide radical, and benzyl is removed by catalytic hydrogenation reaction; finally, the chiral resolution is carried out to obtain a target product. The (S)-3-phenylpiperidine can be synthesized according to the synthesis method. (S)-3-p-aminosalicylic phenylpiperidine can be synthesized according to the third aspect; or according to the fourth aspect, (S)-3-p-bromophenyl piperidine is synthesized to serve asthe key intermediate for preparing the niraparib. According to the synthesis method for (R)-3-phenylpiperidine or/ and (S)-3-phenylpiperidine and the synthesis method for chiral intermediate of niraparib, production cost is obviously lowered, and the synthesis methods are favorable for the large-scale industrial production of a niraparib medicine.

Asymmetric Hydrogenation of 3-Substituted Pyridinium Salts

The use of an equivalent amount of an organic base leads to high enantiomeric excess in the asymmetric hydrogenation of N-benzylated 3-substituted pyridinium salts into the corresponding piperidines. Indeed, in the presence of Et3N, a Rh-JosiPhos catalyst reduced a range of pyridinium salts with ee values up to 90 %. The role of the base was elucidated with a mechanistic study involving the isolation of the various reaction intermediates and isotopic labeling experiments. Additionally, this study provided some evidence for an enantiodetermining step involving a dihydropyridine intermediate.