53912-80-4

Basic information

• Product Name: (S)-(-)-1-BENZYL-2-PYRROLIDINEMETHANOL
• Synonyms: (1-Benzyl-2-pyrrolidinyl)methanol;[1-(phenylmethyl)-2-pyrrolidinyl]methanol;[1-(phenylmethyl)pyrrolidin-2-yl]methanol;1-N-Benzyl-L-prolinol;(S)-1-(Phenylmethyl)-2-pyrrolidinemethanol;N-BENZYL-L-PROLINOL;(S)-(1-BENZYL-PYRROLIDIN-2-YL)-METHANOL;S(-)-1-BENZYLPYRROLIDINE-2-METHANOL
• CAS NO: 53912-80-4
• Molecular Formula: C₁₂H₁₇NO
• Molecular Weight: 191.27
• Mol File: 53912-80-4.mol
• Article Data: 31

Chemical Properties

• Boiling Point: 115-120 °C0.5 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: light yellow liquid
• Density: 1.08 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.000213mmHg at 25°C
• Refractive Index: n20/D 1.541(lit.)
• Storage Temp.: 2-8°C
• PKA: 14.77±0.10(Predicted)
• BRN: 3663640
• CAS DataBase Reference: (S)-(-)-1-BENZYL-2-PYRROLIDINEMETHANOL(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(-)-1-BENZYL-2-PYRROLIDINEMETHANOL(53912-80-4)
• EPA Substance Registry System: (S)-(-)-1-BENZYL-2-PYRROLIDINEMETHANOL(53912-80-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• F: 3-10-34
• HazardClass: IRRITANT
• Hazardous Substances Data: 53912-80-4(Hazardous Substances Data)

Usage

Description

(S)-(-)-1-Benzyl-2-pyrrolidinemethanol, also known as (S)-BPPM, is a chiral secondary alcohol with a benzyl group attached to the first carbon and a pyrrolidine ring at the second carbon. It is a colorless to pale yellow liquid and is commonly used as a precursor in the synthesis of various organic compounds, particularly those with biological activity.

Uses

Used in Pharmaceutical Industry:
(S)-(-)-1-Benzyl-2-pyrrolidinemethanol is used as a precursor for the synthesis of proline-derived homochiral amine oxides, which are important building blocks in the development of pharmaceuticals with potential applications in treating various diseases.
Used in Natural Products Synthesis:
(S)-(-)-1-Benzyl-2-pyrrolidinemethanol serves as a starting material for the synthesis of enantiomerically pure 3-hydroxypiperidine, a structural feature that is present in many natural products. This makes it a valuable compound in the field of natural product chemistry, where the development of novel bioactive compounds is of great interest.
Used in Chiral Chemistry:
Due to its chiral nature, (S)-(-)-1-Benzyl-2-pyrrolidinemethanol is also used in chiral chemistry for the synthesis of enantiomerically pure compounds. These compounds have potential applications in various industries, including pharmaceuticals, agrochemicals, and materials science, where the stereochemistry of molecules plays a crucial role in their biological activity and function.

InChI:InChI=1/C12H17NO/c14-10-12-7-4-8-13(12)9-11-5-2-1-3-6-11/h1-3,5-6,12,14H,4,7-10H2/t12-/m0/s1

Upstream product

• 100-39-0 benzyl bromide 
• 23356-96-9 (S)-1-Pyrrolidin-2-yl-methanol 
• 151265-11-1 (S)-1-benzyl-N,N-dimethylpyrrolidine-2-carboxamide 
• 176240-12-3 (2S)-1-benzylpirrolidine-2-carbaldehyde 
• 100-44-7 benzyl chloride 
• 31795-93-4 N-benzyl-L-proline 
• 98-88-4 benzoyl chloride 
• 344-25-2 D-Prolin 
• 2577-48-2 methyl (2S)-pyrrolidine carboxylate 
• 100-52-7 benzaldehyde 
• 147-85-3 L-proline 
• 113304-84-0 N-benzyl-(S)-proline methyl ester 
• 5874-58-8 N-(benzoyl)-L-proline 

Downstream Products

• 176240-12-3 (2S)-1-benzylpirrolidine-2-carbaldehyde 
• 262428-27-3 (S)-S-[(1-benzylpyrrolidin-2-yl)methyl] ethanethioate 
• 4783-65-7 N-benzyl-2-piperidinone 
• 91599-79-0 (S)-1-N-benzyl-3-hydroxypiperidine 
• 625471-18-3 tert-butyl (3S)-3-aminopiperidine-1-carboxylate 
• 143900-43-0 tert-butyl (3R)-3-hydroxypiperidine-1-carboxylate 
• 1314639-99-0 (S)-1-benzyl-2-(di-tert-butylisobutylsilyloxymethyl)pyrrolidine 
• 1418282-20-8 tert-butyl (3R,2'S,αS)-3-[N-benzyl-N-(α-methylbenzyl)amino]-3-[N(1')-benzylpyrrolidin-2'-yl]propanoate 
• 1418282-22-0 tert-butyl (3S,2'S,αR)-3-[N-benzyl-N-(α-methylbenzyl)amino]-3-[N(1')-benzylpyrrolidin-2'-yl]propanoate 
• 1418282-18-4 tert-butyl (S,E)-3-[N(1')-benzylpyrrolidin-2'-yl]propenoate 
• 112513-33-4 (1R,8S)-(+)-absouline 

Relevant articles and documents

Understanding the Alkylation Mechanism of 3-Chloropiperidines – NMR Kinetic Studies and Isolation of Bicyclic Aziridinium Ions

The present study describes the kinetic analysis of the 3-chloropiperidine alkylation mechanism. These nitrogen mustard-based compounds are expected to react via a highly electrophilic bicyclic aziridinium ion, which is readily attacked by nucleophiles. Halide abstraction using silver salts with weakly coordinating anions lead to the isolation of these proposed intermediates, whereas their structure was confirmed by single crystal XRD. Kinetic studies of the aziridinium ions also revealed notable reactivity differences of the C5 gem-methylated compounds and their unmethylated counterparts. The observed reactivity trends were also reflected by NMR studies in aqueous solution and DNA alkylation experiments of the related 3-chloropiperidines. Therefore, the underlying Thorpe-Ingold effect might be considered as another option to adjust the alkylation activity of these compounds.

Synthesis of Optically Active N -(4-Hydroxynon-2-enyl)pyrrolidines: Key Building Blocks in the Total Synthesis of Streptomyces coelicolor Butanolide 5 (SCB-5) and Virginiae Butanolide A (VB-A)

Starting from 5-methylhexanal and (S)-configured N -propargylprolinol ethers, coupling delivered N -(4-hydroxynon-2-ynyl)prolinol derivatives as mixtures of C4 diastereomers. Resolution of the epimers succeeded after introduction of an (R)-mandelic ester derivative and subsequent HPLC separation. Alternatively, suitable oxidation gave the corresponding alkynyl ketone. Midland reagent controlled diastereoselective reduction afforded a defined configured propargyl alcohol with high selectivity. LiAlH 4reduction and Mosher analyses of the allyl alcohols enabled structure elucidation. The suitably protected products are used as key intermediates in enantioselective Streptomyces γ-butyrolactone signaling molecule total syntheses.

Reduction of N,N-Dimethylcarboxamides to Aldehydes by Sodium Hydride–Iodide Composite

A new and concise protocol for selective reduction of N,N-dimethylamides into aldehydes was established using sodium hydride (NaH) in the presence of sodium iodide (NaI) under mild reaction conditions. The present protocol with the NaH-NaI composite allows for reduction of not only aromatic and heteroaromatic but also aliphatic N,N-dimethylamides with wide substituent compatibility. Retention of α-chirality in the reduction of α-enantioriched amides was accomplished. Use of sodium deuteride (NaD) offers a new step-economical alternative to prepare deuterated aldehydes with high deuterium incorporation rate. The NaH-NaI composite exhibits unique chemoselectivity for reduction of N,N-dimethylamides over ketones.