495-47-6

Upstream product

• 495-47-6 2-(2'-hydroxy-2'-phenylethyl)piperidine 
• 104-55-2 3-phenyl-propenal 
• 1462-92-6 6-methyl-2,3,4,5-tetrahydro-pyridine 
• 100-52-7 benzaldehyde 
• 130721-64-1 (Z)-1-phenyl-2-piperidin-2-ylideneethanone 
• 30800-90-9 1-phenyl-2-(piperidin-2-yl)ethan-1-one 
• 85908-96-9 2-oxopiperidine-1-carboxylic acid tert-butyl ester 
• 76469-99-3 1-(carbomethoxy)-2-phenacylpiperidine 
• 119910-09-7 N-tert-butoxycarbonyl-2-ethoxypiperidine 
• 13735-81-4 1-styrenyloxytrimethylsilane 
• 134040-02-1 (R)-2-((R)-2-Hydroxy-2-phenyl-ethyl)-piperidine-1-carboxylic acid methyl ester 
• 34418-91-2 2,3,4,5-tetrahydropyridine N-oxide 
• 4801-58-5 N-hydroxypiperidine 
• 70546-85-9 2-phenyl-3,3a,4,5,6,7-hexahydro-2H-isoxazolo<2,3-a>pyridine 

Downstream Products

• 934472-23-8 2-(2-hydroxy-2-phenyl-ethyl)-piperidine-1-carboxylic acid benzyl ester 
• 112653-26-6 (1S)-1-Phenyl-2<(2R)-2-piperidyl>ethanol 
• 127983-45-3 6-(2'-hydroxy-2'-phenylethyl)-2,3,4,5-tetrahydropyridine 
• 111612-22-7 (1R)-1-Phenyl-2<(2R)-2-piperidyl>ethanol 
• 1415-36-7 (-)-norsedamine 
• 497-88-1 sedamine 
• 111528-22-4 (1R,3R)-1-(4-Nitro-phenyl)-3-phenyl-hexahydro-pyrido[1,2-c][1,3]oxazine 
• 131697-74-0 (2S,3aR)-8-Benzyl-3a-methyl-2-phenyl-hexahydro-isoxazolo[2,3-a]pyridin-8-ium; bromide 
• 127983-46-4 cis-6-methyl-8-phenyl-9-oxa-1-azabicyclo<4.3.0>nonane 
• 497-89-2 2-[1-methyl-(2S)-piperidin-2-yl]-1-phenyl-(1R)-ethan-1-ol 

Relevant academic research and scientific papers

Decarboxylative Conjunctive Cross-coupling of Vinyl Boronic Esters using Metallaphotoredox Catalysis

The synthesis of complex alkyl boronic esters through conjunctive cross-coupling of vinyl boronic esters with carboxylic acids and aryl iodides is described. The reaction proceeds under mild metallaphotoredox conditions and involves an unprecedented decarboxylative radical addition/cross-coupling cascade of vinyl boronic esters. Excellent functional-group tolerance is displayed, and application of a range of carboxylic acids, including secondary α-amino acids, and aryl iodides provides efficient access to highly functionalized alkyl boronic esters. The decarboxylative conjunctive cross-coupling was also applied to the synthesis of sedum alkaloids.

Stereoselective synthesis of 2-(2-hydroxyalkyl)piperidine alkaloids through prins-ritter reaction

A stereoselective total synthesis of the 2-(2-hydroxyalkyl)piperidine alkaloids has been accomplished by a Prins-Ritter amidation sequence. Other steps involved in this synthesis are Jacobsen's hydrolytic kinetic resolution (HRK) and ring-closing metathes

A rapid access to (±)-sedamine and some original N -benzyl unsaturated analogues

Reduction of N-alkyl-2-(2-hydroxy-2-phenylethyl)pyridinium salts using excess of sodium triacetoxyborohydride afforded exclusively the corresponding tetrahydropyridine derivative bearing a piperidine ring with a double bond in the 3,4-position. Furthermore, under these conditions, syn-1,3-amino alcohols were obtained in good yield and diastereoselectivity. Georg Thieme Verlag Stuttgart · New York.

Studies on the Eschenmoser coupling reaction and insights on its mechanism. Application in the synthesis of Norallosedamine and other alkaloids

The conditions of the Eschenmoser coupling reaction were studied. The formation of the α-thioiminium ion was achieved faster in the presence of an additive (NaI) and dry chloroform as the preferred solvent. The developed conditions were used for the second part of the reaction (the sulfur extrusion itself). The present protocol avoids the formation of byproducts, which were previously described as a major drawback to be overcome. Electrospray ionization tandem mass spectrometry was used to characterize some aspects (intermediates) of the first step of the reaction mechanism. Some reduction conditions were properly tested and the selected conditions were applied to the synthesis of the natural alkaloid Norallosedamine and other derivatives.

An efficient approach to 2-substituted N-tosylpiperdines: asymmetric synthesis of 2-(2-hydroxy substituted)piperidine alkaloids

We have developed an efficient and a general approach to chiral 2-substituted N-tosylpiperidines starting from chiral α-substituted-N-tosylaziridines. Using this approach, we have synthesized (+)-coniine. The synthesis of chiral N-tosyl-2-piperidinylethanol 15 and ent-15, was achieved from l- and d-aspartic acids, respectively in few steps. Piperidine 15 was converted into 2-(2-hydroxysubstituted)piperidines of type 2 in optically active form. By applying this strategy, asymmetric syntheses of halosaline (R,R)-2a, (+)- and (-)-sedamine 2b, (+)- and (-)-allosedamine 2c, (+)- and (-)-sedridine 2d, (+)- and (-)-allosedridine 2e, (+)-tetraponerine T-3 3a, T-4 3c, T-7 3b, and T-8 3d have been achieved in high yields. These stereoisomers can be interconverted via Mitsunobu inversion in excellent yields.

Stereoselective synthesis of (-)-allosedamine

A stereoselective synthesis of (-)-allosedamine is disclosed. β-Aminosulfoxide 4 was generated stereoselectively by condensation of the sulfinyl anion 2 with N-Ts imine 3. The bromohydrin 5 was obtained by intramolecular sulfinyl group participation and the piperidine ring of allosedamine was elaborated using the ring-closing metathesis (RCM) reaction.

Stereoselective synthesis of (-)-allosedamine and (1R,3R)-HPA-12 from β-p-toluenesulfonamido-γ,δ-unsaturated sulfoxide

A stereoselective synthesis of (-)-allosedamine and HPA-12 is disclosed. The key steps of the synthesis include the diastereoselective synthesis of a β-sulfonamido unsaturated sulfoxide, elaboration of a bromohydrin via intramolecular sulfinyl group participation and a ring-closing metathesis reaction for the construction of the piperidine ring of allosedamine.

Diastereoselective, one-pot synthesis of γ-amino alcohols from ketimines

Deprotonation of ketimines with lithium diisopropyl amide, followed by reaction with aldehydes and subsequent reduction with aluminium hydrides gave γ-amino alcohols with moderate to good syn selectivity. The scope and limitations of this preparative meth

A concise synthesis of homochiral sedamines and related alkaloids. A new reductive application of Jacobsen's catalyst

Two methods for the generation of both enantiomers of sedamine [1- methyl-2-(2-phenyl-2-hydroxy-1-ethyl)piperidine] in high optical purity have been elaborated. The first utilises the lipase-mediated kinetic resolution of racemic acetates and the second involves the NaBH4 mediated reduction of ketones catalysed by Jacobsen's catalyst. Some related applications of these reactions are also disclosed.

Trimethylsilyl trifluoromethanesulfonate (TMSOTf) catalyzed amidoalkylation of silylenolethers. Stereocontrolled syntheses of (+/-)-sedamine and (+/-)-norsedamine

Trimethylsilyl trifluoromethanesulfonate (TMSOTf) catalyzed addition of 1-trimethylsilyloxy-1-phenylethene to N-ethoxycarbonyl- and N-tert-butoxycarbonyl-2-ethoxypiperidines (3a and 3b, respectively) afforded the corresponding ketocarbamates 4a and 4b, in excellent yields. Stereoselective conversion to (±)-norsedamine (7) and (±)-sedamine (8) is described.