94944-69-1

Basic information

• Product Name: S-1-CBZ-3-Hydroxy-piperidine
• Synonyms: S-1-CBZ-3-Hydroxy-piperidine;(S)-1-Cbz-3-hydroxy-piper...;(S)-Benzyl 3-hydroxypiperidine-1-carboxylate;benzyl (3S)-3-hydroxypiperidine-1-carboxylate;(3S)-3-Hydroxy-1-piperidinecarboxylic acid phenylmethyl ester;Benzyl (3S)-3-hydroxy-1-piperidinecarboxylate
• CAS NO: 94944-69-1
• Molecular Formula: C₁₃H₁₇NO₃
• Molecular Weight: 235.27898
• Mol File: 94944-69-1.mol

Chemical Properties

• Boiling Point: 384.9±42.0 °C(Predicted)
• Appearance: /
• Density: 1.220±0.06 g/cm3(Predicted)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 14.72±0.20(Predicted)
• CAS DataBase Reference: S-1-CBZ-3-Hydroxy-piperidine(CAS DataBase Reference)
• NIST Chemistry Reference: S-1-CBZ-3-Hydroxy-piperidine(94944-69-1)
• EPA Substance Registry System: S-1-CBZ-3-Hydroxy-piperidine(94944-69-1)

Safety Data

• Hazardous Substances Data: 94944-69-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
S-1-CBZ-3-Hydroxy-piperidine is used as a protecting reagent for amines in the synthesis of pharmaceutical products. Its role is to prevent unwanted reactions during the organic synthesis process, allowing chemists to have better control over the reactions and the resulting compounds.
Used in Organic Synthesis:
S-1-CBZ-3-Hydroxy-piperidine is used as a key component in the construction of complex molecules in organic chemistry. Its CBZ protecting group is crucial for the formation of derivatives, providing a means to protect amines during the synthesis process.
Used in Research and Development:
S-1-CBZ-3-Hydroxy-piperidine is used as a research tool in the development of new pharmaceutical products and organic compounds. Its ability to protect amines and be specifically targeted for removal makes it a valuable asset in the exploration of new chemical reactions and the creation of novel molecules.

InChI:InChI=1S/C13H17NO3/c15-12-7-4-8-14(9-12)13(16)17-10-11-5-2-1-3-6-11/h1-3,5-6,12,15H,4,7-10H2/t12-/m0/s1

Upstream product

• 66207-23-6 1-benzyloxycarbonyl-1,2,3,6-tetrahydropyridine 
• 24211-55-0 (S)-3-hydroxypiperidine 
• 501-53-1 benzyl chloroformate 
• 94944-62-4 (S)-4,5-O-isopropylidene-4,5-dihydroxypentanenitrile 
• 94944-65-7 (S)-N-<(benzyloxy)carbonyl>-5-amino-1,2-pentanediol 
• 330798-20-4 (3S)-2,3-dihydroxypiperidine-1-carboxylic acid benzyl ester 
• 94944-61-3 (S)-N-<(benzyloxy)carbonyl>-1-O-<(4-methylphenyl)sulfonyl>-2-O-(2-tetrahydropyranyl)-5-amino-1,2-pentanediol 
• 94944-66-8 (S)-N-<(benzyloxy)carbonyl>-1-O-<(4-methylphenyl)sulfonyl>-5-amino-1,2-pentanediol 
• 94944-64-6 (S)-N-<(benzyloxy)carbonyl>-1,2-O-isopropylidene-5-amino-1,2-pentanediol 
• 94944-63-5 (S)-1,2-O-isopropylidene-5-amino-1,2-pentanediol 
• 94944-68-0 (S)-N-<(benzyloxy)carbonyl>-3-O-(2-tetrahydropyranyl)-3-piperidinol 

Downstream Products

• 24211-55-0 (S)-3-hydroxypiperidine 
• 167112-99-4 (S)-3-acetoxy-1-(benzyloxycarbonyl)piperidine 
• 1022150-12-4 (R)-3-(4-phenoxyphenyl)-1-(piperidine-3-yl)-1H-pyrazolo[3,4-d]pyrimidine-4-amine 

Relevant articles and documents

Preparation methods and applications of chiral spirophosphine-nitrogen-phosphine tridentate ligand and iridium catalyst thereof

The invention relates to preparation methods and applications of a chiral spirophosphine-nitrogen-phosphine tridentate ligand SpiroPNP and an iridium catalyst Ir-SpiroPNP thereof. The chiral spirophosphine-nitrogen-phosphine tridentate ligand is a compound represented by a formula I, or a racemate or an optical isomer thereof, or a catalytically acceptable salt thereof, and is mainly structurallycharacterized by having a chiral spiro indane skeleton and a phosphine ligand with a large steric hindrance substituent. The chiral spirophosphine-nitrogen-phosphine tridentate ligand can be synthesized by taking a 7-diaryl/alkylphosphino-7'-amino-1,1'-spiro indane compound with a spiro skeleton as a chiral starting raw material. The iridium catalyst of the chiral spirophosphine-nitrogen-phosphinetridentate ligand is a compound represented by a formula II which is described in the specification, or a raceme or an optical isomer, or a catalytically acceptable salt thereof, can be used for catalyzing asymmetric catalytic hydrogenation reaction of carbonyl compounds, particularly shows high yield (greater than 99%) and enantioselectivity (as high as 99.8% ee) in asymmetric hydrogenation reaction of simple dialkyl ketone, and has practical value.

Chemo- And stereodivergent preparation of terminal epoxides and bromohydrins through One-Pot biocatalysed reactions: Access to enantiopure Five- and Six-Membered N-Heterocycles

Different enantiopure terminal epoxides or bromohydrins have chemoselectively been synthesised in one-pot starting from the corresponding a-bromo ketones through alcohol dehydrogenase (ADH)-catalysed processes adding an organic cosolvent and tuning appropriately the medium pH and the temperature. Thus, at neutral pH enantiopure bromohydrins were obtained while using basic conditions (pH 9.5-10) epoxides were isolated as the main product. Furthermore, by simple selection of the biocatalyst, chemo- and stereodivergent transformations were achieved to obtain, e.g., enantiopure prolinol or piperidin-3-ol.

Dihydroxylation of vinyl sulfones: Stereoselective synthesis of (+)- and (-)-febrifugine and halofuginone

(Chemical Equation Presented) The asymmetric dihydroxylation of amino-functionalized vinyl sulfone 19 has been used for the 3-step preparation of 3-hydroxylpiperidine 24 in 86% enantiomeric excess. This enantiomerically enriched building block was used then to synthesize the naturally occurring antimalarial alkaloid febrifugine 1 and its antiangiogenic analogue, halofuginone 3.

Synthesis and antibacterial activity of ketolides (6-O-methyl-3- oxoerythromycin derivatives): A new class of antibacterials highly potent against macrolide-resistant and -susceptible respiratory pathogens

In the search for new antibiotics active against macrolide-resistant pneumococci and Haemophilus influenzae, we synthesized a new class of 3-oxo- 6-O-methylerythromycin derivatives, so-called 'ketolides'. A keto function was introduced in position 3 after removal of L-cladinose, a sugar which has long been thought essential. Further modifications of the macrolactone backbone allowed us to obtain three different series of 9-oxime, 11,12- carbamate, and 11,12-hydrazonocarbamate ketolides. These compounds were found to be very active against penicillin/erythromycin-resistant pneumococci and noninducers of MLS(B) resistance. The 11,-12-substituted ketolide 61 (HMR 3004) demonstrated a potent activity against multiresistant pneumococci associated with a well-balanced activity against all bacteria involved in respiratory infections including H. influenzae, Mycoplasma catarrhalis, group A streptococci, and atypical bacteria. In addition HMR 3004 displayed high therapeutic activity in animals infected by all major strains, irrespective of their resistance phenotype.

Enantioenriched N-(2-Chloroalkyl)-3-acetoxypiperidines as Potential Cholinotoxic Agents. Synthesis and Preliminary Evidence for Spirocyclic Aziridinium Formation.

The syntheses of six enantioenriched analogs representing cyclic forms of acetylcholine are reported. (S)- and (R)-N-(2-chloroethyl)-3-acetoxypiperidine and (R,R)-, (R,S)-, (S,R)-, and (S,S)-N-(2-chloropropyl)-3-acetoxypiperidine have been synthesized from (R)- or (S)-3-hydroxypiperidine in five steps. (R)- and (S)-3-hydroxypiperidine were accessed via parallel stereospecific routes from d- and l-glutamic acid, and through fractional recrystallization of diastereomeric tartranilic acid salts. (S)-N-(2-Chloroethyl)-3-acetoxypiperidine was reacted with silver perchlorate to form a spirocyclic aziridinium analog of acetylcholine as evidenced by a characteristic 1H NMR shift for the aziridinium methylene groups.

Chiral Synthesis via Organoboranes. 6. Hydroboration. 74. Asymmetric Hydroboration of Representative Heterocyclic Olefins with Diisopinocamphenylborane. Synthesis of Heterocyclic Boronates and Heterocyclic Alcohols of Very High Enantiomeric Purity

The hydroboration of representative heterocycles bearing an endocyclic double bond with diisopinocamphenylborane (Ipc2BH) was investigated systematically to establish the asymmetric induction achieved in the reaction.The hydroboration of 2,3- and 2,5-dihydrofurans, 1,4-epoxy-1,4-dihydronaphthalene, and 2,3-dihydrothiophene with Ipc2BH in THF at -25 deg C proceeded very cleanly to afford the corresponding trialkylboranes.These trialkylboranes readily eliminate α-piene on treatment with acetaldehyde to give the corresponding boronates, R*B(OR)2.Oxidation afforded in high yields the corresponding heterocyclic alcohols of 100percent ee.N-(Carbobenzyloxy)-3-pyrroline could not be hydroborated with Ipc2BH below 0 deg C.The oxidation of the intermediate trialkylborane gave N-(carbobenzyloxy)-3-pyrrolidinol in 89percent ee.Similarly, six-membered heterocyclic olefins, namely, 3,4-dihydropyran and 3,4-dihydrothiapyran, were hydroborated with Ipc2BH at 0 deg C in THF.The resulting trialkylboranes on treatment with acetaldehyde followed by oxidation yielded 3-hydroxytetrahydropyran and 3-hydroxytetrahydrothiapyran of 83percent and 66percent ee, respectively.N-(Carbobenzyloxy)-1,2,3,6-tetrahydropyridine, hydroborated with Ipc2BH at 0 deg C, followed by oxidation, afforded the corresponding 3- and 4-piperidinols in an 85:15 ratio.The asymmetric induction achieved during hydroboration was 70percent.The five-membered heterocyclic boronates of very high optical purity, highly versatile synthetic intermediates, were isolated both as the diethyl and the diethanolamine esters.