250249-85-5

Usage

Uses

Used in Pharmaceutical Synthesis:
(R)-1-N-BOC-PIPERIDINE-2-ETHANOL is used as a key intermediate for the synthesis of various pharmaceuticals, leveraging its chiral nature and BOC protecting group to facilitate the creation of enantiopure molecules. The BOC group can be removed under mild conditions, revealing the amino group and allowing for further reactions to produce biologically active compounds.
Used in Organic Synthesis:
In the field of organic synthesis, (R)-1-N-BOC-PIPERIDINE-2-ETHANOL serves as a versatile building block for the preparation of nitrogen-containing compounds. Its structure allows for the synthesis of a wide range of molecules with potential applications in various industries, including the development of new drugs and other bioactive substances.
Used in Chiral Compound Preparation:
(R)-1-N-BOC-PIPERIDINE-2-ETHANOL is used as a crucial intermediate in the preparation of chiral compounds, which are essential in many chemical and pharmaceutical processes. Its chiral center ensures that the final products have the desired stereochemistry, which is critical for their biological activity and efficacy.

InChI:InChI=1/C12H23NO3/c1-12(2,3)16-11(15)13-8-5-4-6-10(13)7-9-14/h10,14H,4-9H2,1-3H3/t10-/m1/s1

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 68419-38-5 (2R)-2-(2-methoxyethyl)piperidine 
• 108-05-4 vinyl acetate 
• 118811-03-3 tert-butyl 2-(2-hydroxyethyl)piperidine-1-carboxylate 
• 893442-85-8 tert-butyl (R)-2-[2-(tert-butyldiphenylsilyloxy)ethyl]piperidine-1-carboxylate 
• 108-55-4 glutaric anhydride, 
• 28697-17-8 N-BOC-D-pipecolic acid 
• 1484-84-0 2(RS)-(2-hydroxyethyl)piperidine 
• 1393603-28-5 C₇H₁₅NO*C₁₀H₁₆O₄S 
• 351410-32-7 (R)-2-(1-(tert-butoxycarbonyl)piperidin-2-yl) acetic acid 
• 813433-73-7 (R)-2-methoxycarbonylmethylpiperidine-1-carboxylic acid tert-butyl ester 
• 639458-46-1 (R)-2-(2-oxo-ethyl)-piperidine-1-carboxylic acid tert-butyl ester 
• 1000806-51-8 (E)-(7-tert-butoxycarbonylamino)-2-heptenal 
• 327158-13-4 (R)-6-Allyl-1-[(R)-1-(2-hydroxy-phenyl)-ethyl]-piperidin-2-one 

Downstream Products

• 351410-32-7 (R)-2-(1-(tert-butoxycarbonyl)piperidin-2-yl) acetic acid 
• 639458-46-1 (R)-2-(2-oxo-ethyl)-piperidine-1-carboxylic acid tert-butyl ester 
• 893429-73-7 tert-butyl (R)-2-[2-(2-nitrophenylselenyl)ethyl]piperidine-1-carboxylate 
• 1202039-12-0 (+)-(2R)-(2-oxopropyl)piperidine-1-carbamic acid tert-butylester 
• 1393603-42-3 C₂₈H₃₃I₂NO₆ 
• 1393603-65-0 C₂₈H₃₃I₂NO₆ 
• 1393603-30-9 (R,E)-tert-butyl-2-(4-(2-iodo-4,5-dimethoxyphenyl)-2-oxobut-3-enyl)piperidine-1-carboxylate 
• 1393603-26-3 C₁₇H₂₂INO₃ 
• 1393603-37-6 (4S,9aR)-hexahydro-4-(2-(2'-methoxymethoxy-5'-carboxaldehyphenyl)-4,5-dimethoxyphenyl)-1H-quinolizin-2(6H)-one 
• 1393603-43-4 (4S,9aR)-hexahydro-4-(2-(2'-methoxymethoxy-5'-methanolphenyl)-4,5-dimethoxyphenyl)-1H-quinolizin-2(6H)-ol 
• 1393603-44-5 (4S,9aR)-hexahydro-4-(2-(2'-methoxymethoxy-5'-carboxaldehyphenyl)-4,5-dimethoxyphenyl)-1H-quinolizin-2(6H)-ol 
• 1393603-47-8 (4S,9aR)-hexahydro-4-(2-(2'-methoxymethoxy-5'-carboxaldehyphenyl)-4,5-dimethoxyphenyl)-1H-quinolizin-2yl-acrylate 
• 1393603-48-9 (4S,9aR)-hexahydro-4-(2-(2'-hydroxy-5'-carboxaldehyphenyl)-4,5-dimethoxy-phenyl)-1H-quinolizin-2yl-acrylate 
• 1393603-50-3 (4S,9aR)-hexahydro-4-(2-(2'-tert-butyldimethylsiloxy-5'-carboxaldehyphenyl)-4,5-dimethoxy-phenyl)-1H-quinolizin-2yl-acrylate 

Relevant academic research and scientific papers

Novel multi-target azinesulfonamides of cyclic amine derivatives as potential antipsychotics with pro-social and pro-cognitive effects

Currently used antipsychotics are characterized by multireceptor mode of action. While antagonism of dopamine D2 receptors is responsible for the alleviation of “positive” symptoms of schizophrenia and the effects at other, particularly serotonergic receptors are necessary for their additional therapeutic effects, there is no consensus regarding an “ideal” target engagement. Here, a detailed SAR analysis in a series of 45 novel azinesulfonamides of cyclic amine derivatives, involving the aryl-piperazine/piperidine pharmacophore, central alicyclic amine and azinesulfonamide groups has led to the selection of (S)-4-((2-(2-(4-(benzo[b]thiophen-4-yl)piperazin-1-yl)ethyl)pyrrolidin-1-yl)sulfonyl)isoquinoline (62). The polypharmacology profile of 62, characterized by partial 5-HT1AR agonism, 5-HT2A/5-HT7/D2/D3R antagonism, and blockade of SERT, reduced the “positive”-like, and “negative”-like symptoms of psychoses. Compound 62 produced no catalepsy, demonstrated a low hyperprolactinemia liability and displayed pro-cognitive effects in the novel object recognition task and attentional set-shifting test. While association of in vitro features with the promising in vivo profile of 62 is still not fully established, its clinical efficacy should be verified in further stages of development.

Asymmetric synthesis of (+)-vertine and (+)-lythrine

The total syntheses of the Lythracea alkaloids (+)-vertine and (+)-lythrine are described. Enantioenriched pelletierine is used as a chiral building block and engaged into a two step pelletierine condensation leading to two quinolizidin-2-one diastereomers in a 8:1 ratio. The major product is used in the synthesis of (+)-vertine via aryl-aryl coupling and ring closing metathesis to provide a Z-alkene α to the lactone carbonyl function. The same procedure was used for (+)-lythrine after base induced epimerization of the main quinolizidin-2-one diastereomer. Alternative classical ring closure strategies like macrolactonisation or aryl-aryl coupling failed.

Organocatalytic enantioselective synthesis of quinolizidine alkaloids (+)-myrtine, (-)-lupinine, and (+)-epiepiquinamide

The organocatalytic synthesis of quinolizidine alkaloids (+)-myrtine, (-)-lupinine, and (+)-epiepiquinamide is described. It involved, as the key step, an enantioselective intramolecular aza-Michael reaction (IMAMR) catalyzed by J?rgensen catalyst I, affording the common precursor with high enantioselectivity. This compound was subsequently transformed into the three alkaloids in a highly diastereoselective manner.

Enantioselective organocatalytic intramolecular aza-Michael reaction: A concise synthesis of (+)-sedamine, (+)-allosedamine, and (+)-coniine

(Chemical Equation Presented) The intramolecular aza-Michael reaction of carbamates bearing remote α,β-unsaturated aldehydes under organocatalytic conditions took place with good yields and excellent ee's when Jorgensen catalyst IV was used in the process, giving rise to the enantioselective formation of several five- and six-membered heterocycles. The developed methodology was applied to the synthesis of three piperidine alkaloids.

Synthesis of an optically pure synthetic intermediate of aloperine from a yeast-reductive product

Optically pure (S)- and (R)-vinylpiperidine 2 and (S)-and (A)-(hydroxyethyl)piperidine 3, which were key intermediates for the synthesis of aloperine, were synthesized from yeast-reductive products.

Enzyme assisted enantioselective synthesis of the alkaloid (+)-aloperine

The enantioselective synthesis of the lupinine alkaloid (+)-aloperine is described. The synthetic scheme presents three steps that are mediated by enzymes: kinetic resolution, oxidation of a primary alcohol to an aldehyde and oxidation of a secondary alco

Remote Stereocenter Discrimination in the Enzymatic Resolution of Piperidine-2-ethanol. Short Enantioselective Synthesis of Sedamine and Allosedamine

Kinetic resolution of N-Boc-piperidine-2-ethanol (2), a case of remote stereocenter discrimination, was accomplished by sequential transesterification mediated by two enzymes, Lipase PS and porcine pancreatic lipase, showing opposite enantioselectivity. The gram-scale availability of the two enantiomeric N-Boc alcohols 2a (R) and 2c (S) enlarges their synthetic exploitation for the enantioselective preparation of piperidine alkaloids. As an example, the convenient three-step synthesis of both the enantiomers of sedamine and allosedamine is described.

Total synthesis of (-)-stellettamide B and determination of its absolute stereochemistry.

[figure: see text] The first total synthesis of (-)-stellettamide B has been achieved by a sequence based on amide coupling of the chiral 1-(aminomethyl)-indolizidine fragment, prepared by TiCl4-mediated asymmetric allylation of the tricyclic N-acyl-N,O-a

Investigation of the 4-O-alkylamine substituent of non-peptide quinolone GnRH receptor antagonists

Synthesis and in vitro activity of the enantiomers of quinolone GnRH antagonist (±)-1 are reported. Chiral amino alcohols were prepared from the appropriate cyclic D- or L-amino acids by the Arndt-Eistert homologation followed by reduction of the resulting esters. Incorporation of these pharmacophores was achieved via a novel Mitsunobu alkylation of 4-hydroxyquinolones. The key amine pharmacophore for binding to the rat GnRH receptor was most active in the S-configuration. Ring size was not important for potency with 4, 5, 6, and 7-membered ring amines exhibiting similar potency.