100243-39-8

Basic information

• Product Name: (S)-3-Hydroxypyrrolidine
• Synonyms: (S)-3-PYRROLIDINOL (S)-3-HYDROXYPYRROLIDINE;(S)-(-)-3-PYRROLIDINOL;(S)-3-PYRROLIDINOL;(S)-(-)-3-HYDROXYPYRROLIDINE;(S)-3-HYDROXYPYRROLIDINE;S-HP;(S)-PYRROLIDIN-3-OL;(R)-3-HYDROXYPYRROLIDINE 2-BUTENEDIOATE
• CAS NO: 100243-39-8
• Molecular Formula: C₄H₉NO
• Molecular Weight: 87.12
• EINECS: -0
• Product Categories: Alcohols, Hydroxy Esters and Derivatives;Chiral Compounds;pharmacetical;Chiral Building Blocks;Simple Alcohols (Chiral);Synthetic Organic Chemistry;Pyrrolidines ,Pyrroles
• Mol File: 100243-39-8.mol
• Article Data: 44

Chemical Properties

• Melting Point: 15°C
• Boiling Point: 108-110 °C (8 mmHg)
• Flash Point: >110°C
• Appearance: Clear light yellow to yellow/Liquid After Melting
• Density: 1.078 g/mL at 20 °C(lit.)
• Vapor Pressure: 0.018mmHg at 25°C
• Refractive Index: n20/D 1.490
• Storage Temp.: 2-8°C
• PKA: 14.91±0.20(Predicted)
• Water Solubility: Fully miscible in water.
• Sensitive: Air Sensitive & Hygroscopic
• BRN: 4652606
• CAS DataBase Reference: (S)-3-Hydroxypyrrolidine(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-3-Hydroxypyrrolidine(100243-39-8)
• EPA Substance Registry System: (S)-3-Hydroxypyrrolidine(100243-39-8)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-40
• Safety Statements: 26-37/39-36-22
• WGK Germany: 3
• F: 10-34
• Hazardous Substances Data: 100243-39-8(Hazardous Substances Data)

Usage

Description

(S)-3-Hydroxypyrrolidine, also known as (S)-(-)-3-Hydroxypyrrolidine, is an organic compound that serves as a crucial intermediate in various chemical syntheses. It is characterized by its clear light yellow to yellow liquid appearance after melting. This chiral molecule is essential in the production of various pharmaceuticals, agrochemicals, and dyes due to its unique structural properties and reactivity.

Uses

Used in Pharmaceutical Industry:
(S)-3-Hydroxypyrrolidine is used as a key intermediate for the synthesis of various pharmaceutical compounds. Its chiral nature allows for the creation of enantiomerically pure drugs, which is crucial in ensuring the desired therapeutic effects and minimizing potential side effects.
Used in Agrochemical Industry:
In the agrochemical sector, (S)-3-Hydroxypyrrolidine is utilized as a vital building block in the development of novel agrochemicals. Its incorporation into these compounds can lead to improved efficacy, selectivity, and reduced environmental impact.
Used in Dye Industry:
(S)-3-Hydroxypyrrolidine is employed as a raw material in the synthesis of various dyes. Its unique chemical properties enable the production of dyes with specific color characteristics and improved performance in different applications.
Used in Organic Synthesis:
As an important intermediate in organic synthesis, (S)-3-Hydroxypyrrolidine is used to construct a wide range of complex organic molecules. Its versatility in chemical reactions allows for the development of new compounds with diverse applications in various industries.

Purification Methods

The (±)-isomer is purified by repeated distillation ( b 102-104o/12mm, 108-110o/18mm), and the (±)-picrate crystallises from EtOH with m 140-141o. The R(+)-enantiomer has b 70o/0.6mm and [] D +5.6o (c 3.63, MeOH). Its hydrochloride has a negative rotation and its dimethiodide has m 230o and [] 24 -8.02o. [Suyama & Kanno Yakugaku Zasshi (J Pharm Soc Japan) 85 531 1965, Uno et al. J Heterocycl Chem 24 1025 1987, Flanagan & Joullie Heterocycles 26 2247 1987, Beilstein 21 III/IV 44.]

InChI:InChI=1/C4H9NO/c6-4-1-2-5-3-4/h4-6H,1-3H2/p+1/t4-/m0/s1

Upstream product

• 30724-02-8 (4R)-4-hydroxyproline 
• 84367-31-7 (R)-γ-chloro-β-hydroxybutyronitrile 
• 111466-53-6 (S)-3-((trimethylsilyl)oxy)pyrrolidin-2-one 
• 127913-44-4 (S)-4-chloro-3-hydroxy butyronitrile 
• 1104643-25-5 (S)-3-tert-butoxypyrrolidine 
• 920753-45-3 4-amino-1-bromo-(S)-2-butanol bromide 
• 34368-52-0 (S)-3-hydroxypyrrolidin-2-one 
• 135870-56-3 (S)-3-hydroxy-4-(methanesulfonyloxy)butylamine hydrochloride 
• 135681-60-6 (S)-3-hydroxy-4-(methanesulfonyloxy)butyronitrile 
• 118712-64-4 (S)-3-hydroxy-4-(p-toluenesulfonyloxy)butyronitrile 
• 3398-22-9 trans-4-hydroxyproline 
• 101385-90-4 (S)-N-benzyl-3-hydroxypyrrolidine 
• 101469-91-4 (3S)-1-benzyl-3-hydroxypyrrolidine-2,5-dione 
• 36901-86-7 cis-hydroxy-D-proline 

Downstream Products

• 101385-90-4 (R)-N-benzyl-3-hydroxypyrrolidine 
• 216666-99-8 (R)-1-(2-methoxyethyl)-3-hydroxypyrrolidine 
• 216667-19-5 (R)-1-(o-methoxyphenylmethyl)-3-hydroxypyrrolidine 
• 936482-52-9 C₂₄H₃₀F₃N₅O₃ 

Relevant articles and documents

Further evidence on the PET cyclization of α-silylmethylamines tethered with non-activated olefins: Demonstration by the total synthesis of (-)-retronecanol

The total synthesis of (-)-retronecanol, in order to provide convincing evidence for the PET cyclization of α-trimethylsilylmethyl amines with tethered non-activated olefins, is reported.

Synthesis of (3R)-carboxy pyrrolidine (a β-proline analogue) and its oligomer

A decamer of a β-amino acid analogue of L-proline, (3R)-carboxy pyrrolidine (β-proline), was synthesized from a readily available (R)-glycidol. It was found to possess a rigid secondary structure, as evidenced by its CD spectrum. The β-proline decamer, however, failed to bind to profilin, whereas the corresponding α-L-proline decamer bound tightly to this protein. (C) 2000 Published by Elsevier Science Ltd.

A NOVEL DECARBOXYLATION OF α-AMINO ACIDS. A FACILE METHOD OF DECARBOXYLATION BY THE USE OF 2-CYCLOHEXEN-1-ONE AS A CATALYST

In the presence of a catalytic amount of 2-cyclohexen-1-one, decarboxylation of α-amino acids proceeds smoothly and affords the corresponding amino compounds in good yields.Optically active amino compounds, (3R)-(-)-3-hydroxypyrrolidine and (2R)-(-)-2-hydroxypropylamine are obtained in 93percent and 80percent yields, respectively.

Enzymatic ammonolysis of ethyl (±)-4-chloro-3-hydroxybutanoate. Chemoenzymatic syntheses of both enantiomers of pyrrolidin-3-ol and 5- (chloromethyl)-1,3-oxazolidin-2-one

Lipase B from Candida antarctica efficiently catalysed the kinetic resolution of ethyl (±)-4-chloro-3-hydroxybutanoate through an ammonolysis reaction. Using this methodology, both enantiomers of 4-chloro-3- hydroxybutanamide were prepared and converted into pyrrolidin-3-ol and 5- (chloromethyl)-1,3-oxazolidin-2-one by simple processes consisting of a reduction reaction and a Hofmann rearrangement, respectively.

Synthesis of racemic and enantiomeric 3-pyrrolidinyl derivatives of nucleobases

The synthesis of novel 3-pyrrolidinyl derivatives of nucleobases is described. Starting from malic acid, we improved the synthesis of both racemic and optically active N-benzyl-3-hydroxypyrrolidine-2,5-diones, which were transformed in four steps into N-tert-butyloxycarbonyl-3-mesyloxypyrrolidines, the key synthons for the alkylation of purine and pyrimidine nucleobases. Alkylations of cesium salts of purines and sodium salts of pyrimidines with N-tert-butyloxycarbonyl-3-mesyloxypyrrolidines proceeded smoothly, giving high yields of 9-substituted purine derivatives and moderate yields of 1-substituted pyrimidine derivatives. Using (S)-N-tert-butyloxycarbonyl-3-mesyloxypyrrolidine as the same intermediate for the synthesis of both enantiomeric N-Boc-3-pyrrolidinyladenines, and considering the results obtained on chiral HPLC analysis of the products, we proved that nucleophilic displacement of the mesyloxy group proceeded with inversion and not with retention of the configuration. Prepared compounds were tested for cytostatic and antiviral properties, but no significant activity was found.

Redox Condensations of o-Nitrobenzaldehydes with Amines under Mild Conditions: Total Synthesis of the Vasicinone Family

A total synthesis of the vasicinone family of natural products from bulk chemicals was developed. Reductive condensation of o-nitrobenzaldehydes with amines utilizing iron pentacarbonyl as a reducing agent followed by subsequent oxidation leads to a great variety of polycyclic nitrogen-containing heterocycles under mild conditions. Enantiomerically pure vasicinone, rutaecarpine, isaindigotone, and luotonin were synthesized from readily available starting materials like hydroxyproline, nitrobenzaldehyde, pyrrolidine, and piperidine in two to four operational steps without chromatography. The antifungal activity of all products was tested.

A practical procedure for reduction of primary, secondary and tertiary amides to amines

A mild and general procedure for reduction of primary, secondary, and tertiary amides using catalytic triruthenium dodecacarbonyl and 1,1,3,3-tetramethyldisiloxane as reductant is described. The reaction is tolerant of numerous functional groups, and the amine products can often be isolated by direct crystallization as hydrochloride salts. The catalyst and silane are commercially available, air stable, and inexpensive, making the procedure accessible for both laboratory and large-scale applications. Copyright