66893-75-2

Upstream product

• 67-56-1 methanol 
• 3742-91-4 N-(benzyloxycarbonyl)piperidine 
• 69622-67-9 benzyl 2-hydroxypiperidine-1-carboxylate 
• 106412-35-5 N-benzyloxycarbonyl-2-piperidone 
• 1227635-49-5 α-benzyl-N-benzyloxycarbonylpiperidine 

Downstream Products

• 73269-82-6 2-(5-Fluoro-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-piperidine-1-carboxylic acid benzyl ester 
• 80953-71-5 3,4,5,6,5',6'-Hexahydro-2H,4'H-[2,3']bipyridinyl-1,1'-dicarboxylic acid dibenzyl ester 
• 69622-67-9 benzyl 2-hydroxypiperidine-1-carboxylate 
• 68471-58-9 1-(benzyloxycarbonyl)-1,2,3,4-tetrahydropyridine 

Relevant academic research and scientific papers

Fragment-oriented synthesis: β-elaboration of cyclic amine fragments using enecarbamates as platform intermediates

A strategy for the β-sp3 functionalisation of cyclic amines is described. Regioselective conversion of protected amines to enecarbamates is achieved through electrochemical oxidation; these intermediates can be derivatised by functionalised alkyl halides under photoredox catalysis. The potential of the methods is highlighted by direct growth of a DCP2B-binding fragment. This journal is

Expedient preparation of nazlinine and a small library of indole alkaloids using flow electrochemistry as an enabling technology

An expedient synthesis of the indole alkaloid nazlinine is reported. Judicious choice of flow electrochemistry as an enabling technology has permitted the rapid generation of a small library of unnatural relatives of this biologically active molecule. Furthermore, by conducting the key electrochemical Shono oxidation in a flow cell, the loading of electrolyte can be significantly reduced to 20 mol % while maintaining a stable, broadly applicable process.

Diastereoselective synthesis of 3-fluoro-2-substituted piperidines and pyrrolidines

A facile procedure for synthesis of trans-3-fluoro-2-substituted piperidines by utilizing electrophilic fluorination of cyclic enamines and Lewis acid mediated nucleophilic substitution has been developed. Also, optically active trans-2-allyl-3-fluorinate

Electrochemical deallylation of α-allyl cyclic amines and synthesis of optically active quaternary cyclic amino acids

Electrochemical oxidation of α-allylated and α-betizylated N-acylated cyclic amines by using a graphite anode easily affords the corresponding α-methoxylated products with up to 76% yield. Ease of oxidation was affected by the type of electrode, the size

Stereoselective synthesis of 3-deoxy-piperidine iminosugars from l-lysine

A new method using electrochemical oxidation and/or OsO4 oxidation has been used for the stereoselective synthesis of 2,3,6-trihydroxylated (5S)-piperidine derivatives. The electrochemical method was successively used for the conversion of N-pr

Reactions of iminium ions with Michael acceptors through a Morita-Baylis-Hillman-type reaction: Enantiocontrol and applications in synthesis

(Chemical Equation Presented) All adducts one way: Iminium ions, generated in situ from the corresponding N,O-acetals, can be used as electrophiles in a Morita-Baylis-Hillman-type reaction with a wide range of Michael acceptors (enones, enals, S- and O-acrylates). The reaction has been rendered asymmetric using sulfide 1 (see scheme; DBU = 1,8-diazabicyclo[5.4.0]undec-7-ene, TMSOTf=trimethylsilyl trifluoromethanesulfonate).

Stereoselective synthesis of azasugars by electrochemical oxidation

A new method using electrochemical oxidation has been exploited for the stereoselective synthesis of 2,3,6-trihydroxylated 5S-piperidine derivatives. The electrochemical method was successively used for the conversion of N-protected piperidines to N-prote

Efficient synthesis of piperidine derivatives. Development of metal triflate-catalyzed diastereoselective nucleophilic substitution reactions of 2-methoxy- and 2-acyloxypiperidines

Nucleophilic substitution reactions of 2-methoxy- and 2-acyloxypiperidines were investigated. First, new and efficient methods for the preparation of the starting piperidine derivatives were developed. N-Benzyloxycarbonyl-2-methoxypiperidine (3) and 3-substituted-2-acyloxy-N-benzyloxycarbonylpiperidines (4a-d), which are recognized as the simplest imino-sugars, were prepared and were examined as substrates for nucleophilic substitution reactions with silyl enolates under the influence of catalytic amounts of metal triflates (Sc(OTf)3, Sn(OTf)2, Cu(OTf)2, Hf(OTf)4, etc). Among the triflates tested, Sc(OTf)3 gave the best results. It was found that 2-acetoxy-3-benzyloxy-N-benzyloxycarbonylpiperidine (4a) reacted with silyl enolates to afford the 2-alkylated adducts in high cis-selectivity, while 2,3-diacyloxy-N-benzyloxycarbonylpiperidines (4b-d) showed trans-selectivity. The stereochemical assignments were carefully performed using NMR analysis, X-ray crystallography, and synthetic transformations. Febrifugine (1), a potent antimalarial alkaloid, was successfully synthesized from 2,3-diacetoxy-N-benzyloxycarbonylpiperidine (4b) on the basis of these diastereoselective nucleophilic substitution reactions.

Electroorganic Chemistry. Part 80. α-Hydroxylation of N-Acylated Cyclic Amines and Utilization of the Products as Amino Aldehyde Equivalents

A general method for the transformation of N-acylated cyclic amines (1) to amino aldehydes (4) was exploited.N-Benzoyl- or N-alkoxycarbonyl-α-methoxyamines (2) were prepared by anodic reaction of (1) in methanol.Treatment of (2) with dilute hydrochloric acid gave the corresponding α-hydroxylated compounds (3) which are amino aldehydes equivalents.The reaction of (3) with methoxycarbonylmethylenetriphenylphosphorane yielded ω-amino-α,β-unsaturated esters in satisfactory yields.