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

Chemical Properties

Colorless to pale yellow liquid

Uses

Precursor in the synthesis of proline-derived homochiral amine oxides. Starting material for enantiomerically pure 3-hydroxypiperidine, a structural feature present in many natural products.

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

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

Downstream Products

• 143746-15-0 2,2,4,4-Tetramethyl-oxazolidine-3-carboxylic acid (S)-1-benzyl-pyrrolidin-2-ylmethyl ester 
• 479253-15-1 (2'S)-2-[(1'-benzyl-pyrrolidinyl-2')methoxy]dinaphtho[2,1-d:1',2'-f](1,3,2) dioxaphosphepine 
• 462102-50-7 [(2S)-1-benzylpyrrolidin-2-yl]methyl bis(2,6-dimethylphenyl) phosphite 
• 128574-35-6 (S)-1-Benzyl-2-chloromethyl-pyrrolidine 
• 787564-48-1 (S)-N-benzyl-2-fluoromethylpyrrolidine 
• 873221-82-0 (R)-1-benzyl-3-fluoro-piperidine 
• 262428-27-3 (S)-S-[(1-benzylpyrrolidin-2-yl)methyl] ethanethioate 
• 909806-25-3 [(1R),1(2S)]-S-[(1-benzylpyrrolidin-2-yl)-1-(tert-butyldimethylsilyl)methyl] 2,2,4,4-tetramethyl-oxazolidine-3-carbothioate 
• 909806-20-8 [(1S),1(2S)]-S-[(1-benzylpyrrolidin-2-yl)propyl] 2,2,4,4-tetramethyl-oxazolidine-3-carbothioate 
• 909806-27-5 [(1S),1(2S)]-S-[(1-benzylpyrrolidin-2-yl)-2-phenylethyl] 2,2,4,4-tetramethyl-oxazolidine-3-carbothioate 

Relevant articles and documents

l -Proline as a Valuable Scaffold for the Synthesis of Novel Enantiopure Neonicotinoids Analogs

In this research, six neonicotinoid analogs derived from l-proline were synthesized, characterized, and evaluated as insecticides against Xyleborus affinis. Most of the target compounds showed good to excellent insecticidal activity. To the best of our knowledge, this is the first report dealing with the use of enantiopure l-proline to get neonicotinoids. These results highlighted the compound 9 as an excellent candidate used as the lead chiral insecticide for future development. Additionally, molecular docking with the receptor and compound 9 was carried out to gain insight into its high activity when compared to dinotefuran. Finally, the neurotoxic evaluation of compound 9 showed lower toxicity than the classic neonicotinoid dinotefuran.

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.