24211-55-0

Basic information

• Product Name: (S)-3-Hydroxypiperidine
• Synonyms: (S)-3-Hydroxypiperidine;(3S)-piperidin-3-ol;(S)-Piperidin-3-ol
• CAS NO: 24211-55-0
• Molecular Formula: C₅H₁₁NO
• Molecular Weight: 101.14694
• Mol File: 24211-55-0.mol

Chemical Properties

• Boiling Point: 191.9±23.0 °C(Predicted)
• Appearance: /
• Density: 1.016±0.06 g/cm3(Predicted)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 14.91±0.20(Predicted)
• CAS DataBase Reference: (S)-3-Hydroxypiperidine(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-3-Hydroxypiperidine(24211-55-0)
• EPA Substance Registry System: (S)-3-Hydroxypiperidine(24211-55-0)

Safety Data

• Hazardous Substances Data: 24211-55-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(S)-3-Hydroxypiperidine is used as a key building block for the design and production of drugs, owing to its unique structural and stereochemical attributes. Its specific molecular orientation, indicated by the (S)-3 prefix, can influence the compound's chemical behavior, bioavailability, and efficacy in various pharmaceutical applications.
Used in Organic Synthesis:
(S)-3-Hydroxypiperidine is used as a crucial intermediate in the synthesis of various organic compounds. Its heterocyclic nature and specific molecular orientation make it a valuable component in the creation of complex molecules and structures in organic chemistry.
Used in Medicinal Chemistry Research:
(S)-3-Hydroxypiperidine is used as a research compound in medicinal chemistry, where its properties and reactivity are studied to understand its potential applications in drug discovery and development. Its unique stereochemistry and molecular orientation can provide insights into the design of new therapeutic agents.

Upstream product

• 6859-99-0 3-hydroxypiperazine 
• 24211-54-9 (S)-5-hydroxypiperidin-2-one 
• 94944-69-1 (S)-3-hydroxypiperidine-N-carboxylate benzyl ester 
• 32780-06-6 (5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran 
• 94944-62-4 (S)-4,5-O-isopropylidene-4,5-dihydroxypentanenitrile 
• 24211-53-8 (S)-(+)-5-Azidomethyl-2-oxotetrahydrofuran 
• 58879-34-8 (S)-5-tosyloxypentan-4-olide 
• 94944-63-5 (S)-1,2-O-isopropylidene-5-amino-1,2-pentanediol 
• 94944-65-7 (S)-N-<(benzyloxy)carbonyl>-5-amino-1,2-pentanediol 
• 94944-64-6 (S)-N-<(benzyloxy)carbonyl>-1,2-O-isopropylidene-5-amino-1,2-pentanediol 
• 94944-68-0 (S)-N-<(benzyloxy)carbonyl>-3-O-(2-tetrahydropyranyl)-3-piperidinol 
• 94944-66-8 (S)-N-<(benzyloxy)carbonyl>-1-O-<(4-methylphenyl)sulfonyl>-5-amino-1,2-pentanediol 
• 1451214-33-7 (1’R,2S)-1-(2’-benzyloxy-1’-phenylethyl)-2-(2-[1,3]dioxolan-2-ylethyl)aziridine 
• 1451214-37-1 (1S,1’R)-1-[(2’-benzyloxy-1’-phenylethylamino)methyl]-3-[1,3]dioxolan-2-ylpropyl acetate 

Downstream Products

• 91599-79-0 (S)-1-N-benzyl-3-hydroxypiperidine 
• 94944-69-1 (S)-3-hydroxypiperidine-N-carboxylate benzyl ester 
• 119065-61-1 (R,S)-Benidipine 
• 119065-61-1 (S,S)-Benidipine 
• 1232057-68-9 C₂₄H₃₁Cl₂N₅O₂ 
• 1430810-32-4 (S)-1-(4-(3-hydroxypiperidin-1-ylsulfonyl)phenyl)pyrrolidin-2-one 
• 1430810-49-3 (S)-1-(4-iodophenylsulfonyl)piperidin-3-ol 
• 1443118-52-2 C₂₁H₂₁NO₃ 
• 1450723-70-2 C₁₂H₁₈N₂O₃S 
• 1450724-27-2 C₁₉H₂₁N₃O₇S 
• 1450723-47-3 N-[[4-[[(3S)-3-hydroxy-1-piperidyl]sulfonyl]phenyl]methyl]-1,3-dihydropyrrolo[3,4-c]pyridine-2-carboxamide 
• 1450723-76-8 C₁₂H₁₄N₂O₃S 

Relevant articles and documents

Preparation method of (S)-3-hydroxypiperidine

The invention discloses a preparation method of (S)-3-hydroxypiperidine. The preparation method comprises the steps of (1) carrying out catalytic hydrogenation on 3-hydroxypyridine to prepare 3-hydroxypiperidine; (2) splitting the 3-hydroxypiperidine for preparing the (S)-3-hydroxypiperidine, wherein catalytic hydrogenation is carried out under the co-catalysis of a ruthenium/silicon dioxide catalyst and a cocatalyst; the weight ratio of the ruthenium/silicon dioxide catalyst to the cocatalyst is 1:1 to 3:1; the total weight of the ruthenium/silicon dioxide catalyst and the cocatalyst is 5 to10 percent of the weight of the 3-hydroxypiperidine; and the cocatalyst is aluminum oxide. According to the method provided by the invention, the ruthenium/silicon dioxide catalyst and the aluminum oxide are adopted as a compound catalyst for catalytic hydrogenation, and the compound catalyst is relatively cheap but has the same better catalysis effect, and pollutes environment less so as to be suitable for industrial production.

(S)-1-Boc-3-hydroxypiperidine synthesis method

The invention discloses a (S)-1-Boc-3-hydroxypiperidine synthesis method. The method utilizes (R)-glyceraldehyde acetonide as a raw material. Through witting reaction-based acetonitrile group addition, palladium-carbon-based double bond reduction, deprotection, p-tosyl selective addition, Raney nickel-based hydrogenation reduction of the nitrile group along with ring closing, and piperidine ring nitrogen Boc protection, the (S)-1-Boc-3-hydroxypiperidine is obtained. The method utilizes the cheap chiral raw material as a starting material, produces a chiral product and prevents large material consumption and a yield loss of a splitting technology.

Concise Enantioselective Synthesis of Naturally Active (S)-3-Hydroxypiperidine

A short and efficient enantioselective synthesis of natural product (S)-3-hydroxypiperidine has been achieved starting from commercially available raw materials employing two catalytic routes: (i) cocatalyzed hydrolytic kinetic resolution (HKR) of racemic methyl-3-(oxiran-2-yl)propanoate; (ii) proline-catalyzed α-aminooxylation followed by Horner-Wardsworth-Emmons olefination in high enantiomeric purity (97% ee) and high overall yield (38%). (Chemical Equation Presented).

A practical and enantiospecific synthesis of (-)-(R)- and (+)-(S)-piperidin-3-ols

A highly enantiospecific, azide-free synthesis of (-)-(R)- and (+)-(S)-piperidin-3-ol in excellent yield was developed. The key step of the synthesis involves the enantiospecific ring openings of enantiomerically pure (R)- and (S)-2-(oxiran-2-ylmethyl)-1H-isoindole-1,3(2H)-diones with the diethyl malonate anion and subsequent decarboxylation.

Asymmetric syntheses of pyrrolidine and piperidine derivatives Via regio-and stereo-selective ring-opening reactions of chiral aziridine

Asymmetric synthesis of cyclic β-amino alcohols (pyrrolidine and piperidine derivatives) has been achieved using a chiral aziridine as the starting material. The key step of this synthetic methodology is regio- and stereo-controlled ring-opening of the chiral aziridine with acetic acid or acetyl chloride.

Urethane-containing aminosteroid compounds

Urethane-containing amino steroids having the general chemical formula: STR1 wherein a, b, R1, R2, R3, R4, R14 and Z are as defined in the specification. Also disclosed are pharmaceutical composition and the use of the compounds/composition in the treatment of congestive heart failure.

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.

Synthesis and pharmacological activity of stereoisomers of 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic acid methyl 1-(phenylmethyl)-3-piperidinyl ester

1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic acid methyl 1-(phenylmethyl)-3-piperidinyl ester 1, a highly potent calcium antagonist, was separated into stereo- and optical isomers to investigate the differences of antihypertensive activities between them. Fractional crystallization of the hydrochlorides of 1 gave α- and β-diasterioisomers. The α-isomer (benidipine hydrochloride, KW-3049) showed very strong hypotensive effect, but little activity was observed in the β-isomer. From optically resolved 1,4-dihydro-5-methoxycarbonyl-2,6-dimethyl-4-(3-nitrophenyl)-3-pyridi necarboxylic acids 2, and 1-benzyl-3-piperidinols 3, four optical isomers of 1 were synthesized, and their absolute configurations were deduced. The hypotensive activity of (+)-α, namely (S)-(S)-1, was 30 to 100 times stronger than that of (-)-α in intravenously administered spontaneously hypertensive rats.

REACTIONS OF β-SUBSTITUTED AMINES-IV. KINETICS AND STEREOCHEMISTRY OF THE THERMAL REARRANGEMENT OF (S)-2-CHLOROMETYL-1-ETHYLPYRROLIDINE TO (R)-3-CHLORO-1-ETHYLPIPERIDINE, AND THE STEREO-CHEMICAL COURSE OF THEIR REACTIONS WITH NUCLEOPHILES

The rate of the thermal rearrangement of (S)-2-chloromethyl-1-ethylpyrrolidine to (R)-3-chloro-1-ethylpiperidine has been examined at three temperatures in benzene by PMR and polarimetry.The rearrangement was shown to be completely stereospecific and to obey a simple first order law.The calculated Ea, ΔH(excit.) and ΔS(excit.) were 22+/-2 kcal/mole (25 deg C), 21+/-2.5 kcal/mole (25 deg C) and -10+/-2 e.u. (0 deg K) respectively.The effect of solvents having differing dielectric constants was also studied.A transition state 9'a and an ion pair intermediate 3a are suggested for the rearrangement.The stereochemical course of the reactions of (S)-1a, (R)-2a and (S)-2a with hydroxide and methoxide ions have been shown to be 100percent stereospecific with an uncertainity of about 1percent.The absolute configurations of all optically active reactants and products were established by chemical correlations with known compounds or by ORD and chemical inference.The ring opening of both the primary and secondary aziridinium ion positions of 1-azonia-1-ethylbicyclohexane by nucleophiles proceeds entirely by SN2 processes.The conversion of (R)-1-ethyl-3-hydroxypiperidine to (S)-2a*HCl with thionyl chloride in chloroform proceeds by inversion with 4.8percent racemization, whereas the thermal rearrangement of (S)-1a to (R)-2a occurs with complete retention of absolute configuration.