- Synthesis method for (R)-3-phenylpiperidine or/and (S)-3-phenylpiperidine and synthesis method for chiral intermediate of niraparib
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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.
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- Pd-catalyzed asymmetric allylic alkylation with nitromethane using a chiral diaminophosphine oxide: (S,RP)-Ph-DIAPHOX. Enantioselective synthesis of (R)-preclamol and (R)-baclofen
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A Pd-catalyzed asymmetric allylic alkylation with nitromethane using an aspartic acid-derived P-chirogenic diaminophosphine oxide [(S,RP)-Ph-DIAPHOX] is described. This method was successfully applied to enantioselective synthesis of (R)-precla
- Nemoto, Tetsuhiro,Jin, Long,Nakamura, Hiroshi,Hamada, Yasumasa
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p. 6577 - 6581
(2007/10/03)
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- Dynamic kinetic resolution of racemic γ-aryl-δ-oxoesters. Enantioselective synthesis of 3-arylpiperidines
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Cyclodehydration of racemic γ-aryl-δ-oxoesters with (R)- or (S)-phenylglycinol stereoselectively affords bicyclic δ-lactams, in a process that involves a dynamic kinetic resolution. Subsequent reduction of these lactams leads to enantiopure 3-arylpiperidines. Starting from racemic aldehyde esters, this short sequence has been applied to the synthesis of (R)-3-phenylpiperidine and the antipsychotic drug (-)-3-PPP (an (S)-3-arylpiperidine), whereas starting from racemic ketone esters enantiopure cis-2-alkyl-3-arylpiperidines are prepared.
- Amat, Mercedes,Canto, Margalida,Llor, Nuria,Escolano, Carmen,Molins, Elies,Espinosa, Enrique,Bosch, Joan
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p. 5343 - 5351
(2007/10/03)
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- Dynamic kinetic resolution and desymmetrization of enantiotopic groups by cyclodehydration of racemic or prochiral δ-oxoesters with (R)-phenylglycinol: Enantioselective synthesis of piperidines
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Enantiotopic ester groups are desymmetrized in the cyclodehydration of prochiral δ-oxodiesters with (R)-phenylglycinol. This reaction can be extended to racemic δ-oxodiesters, which undergo a tandem dynamic kinetic resolution-diastereoselective differentiation process (see scheme). The resulting bicyclic lactams can be used in the preparation of a variety of synthetically and pharmacologically interesting enantiopure piperidine derivatives.
- Amat, Mercedes,Canto, Margalida,Llor, Nuria,Ponzo, Viviana,Perez, Maria,Bosch, Joan
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p. 335 - 338
(2007/10/03)
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