1227263-77-5

Basic information

• Product Name: (3S)-1-[(2-aminophenyll)methyl]pyrrolidin-3-ol
• Synonyms: (3S)-1-[(2-aminophenyll)methyl]pyrrolidin-3-ol
• CAS NO: 1227263-77-5
• Molecular Weight: 192.261
• Mol File: 1227263-77-5.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (3S)-1-[(2-aminophenyll)methyl]pyrrolidin-3-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (3S)-1-[(2-aminophenyll)methyl]pyrrolidin-3-ol(1227263-77-5)
• EPA Substance Registry System: (3S)-1-[(2-aminophenyll)methyl]pyrrolidin-3-ol(1227263-77-5)

Safety Data

• Hazardous Substances Data: 1227263-77-5(Hazardous Substances Data)

Usage

General Description

(3S)-1-[(2-aminophenyl)methyl]pyrrolidin-3-ol is a chemical compound with the molecular formula C12H18N2O. It is a pyrrolidine derivative with a hydroxyl group and an amino group attached to the pyrrolidine ring. It is a chiral compound, with the (3S) configuration indicating its stereochemistry. (3S)-1-[(2-aminophenyll)methyl]pyrrolidin-3-ol may have potential pharmaceutical applications due to its structure, which includes both an amine and an alcohol functional group. It may have biological activity as a neurotransmitter, enzyme inhibitor, or other pharmacological function. Further research and testing are necessary to determine its specific properties and potential uses in medicine or other fields.

Upstream product

• 6159-55-3 (+)-vasicinol 

Downstream Products

• 101385-90-4 (S)-N-benzyl-3-hydroxypyrrolidine 
• 486-64-6 (S)-3-hydroxy-2,3-dihydropyrrolo[2,1-b]quinazolin-9(1H)-one 
• 114636-29-2 (3S)-3-azido-1-(phenylmethyl)pyrrolidine 
• 116143-03-4 (3R)-3-azido-1-(phenylmethyl)pyrrolidine 
• 114715-38-7 (3S)-1-benzyl-3-pyrrolidinamine 
• 116183-80-3 (3R)-3-<(4-tolylsulfonyl)oxy>-1-(phenylmethyl)pyrrolidine 

Relevant articles and documents

Synthesis of Ofornine mimics from natural product l-vasicine as anti-hypertensive agents

We report the chemical synthesis of Ofornine mimics from l-vasicine, structure-activity relationship studies and their in vivo screening for anti-hypertensive action in Wistar rats. It was observed that most of the analogs possessed anti-hypertensive effect; however, the duration of the effect was variable and mostly transient. The results demonstrated that the analogs 12, 13, 14, 15, and 16 showed a sharp and significant decrease in systolic and diastolic blood pressure for 30–60 min after intravenous administration. Analog (S)-(3-hydroxypyrrolidin-1-yl)(2-(pyridin-4-ylamino)phenyl)methanone (8) showed a significant decrease in blood pressure in a dose dependent manner whose maximal response lowered to 79.29 ± 4.26 mmHg of SBP and 62.55 ± 2.9 of DBP at 10 mg/kg intravenous dose. Further, the significant anti-hypertensive effect of 8 lasted for about 2.5 h at 10 mg/kg dose. We also evaluated the acute toxicity of the analog 8 as per the OECD guidelines and the compound was found to be safe up to the dose of 2000 mg/kg body weight. These preclinical findings suggest that the analog 8 could be considered as a promising lead and a durable anti-hypertensive drug candidate and deserves further investigation. The SAR studies clearly showed that the amide, hydroxyl and pyridine ring plays important role in showing the activity.

Natural (-)-vasicine as a novel source of optically pure 1-benzylpyrrolidin-3-ol

A facile and scalable methodology for the preparation of optically active (3S)-1-benzylpyrrolidin-3-ol (3), an important drug precursor, is reported. Starting from the naturally occurring alkaloid (-)-vasicine (1), a major alkaloid of the plant Adhatoda vasica, 3 was obtained in 84% overall yield (Scheme 3). Copyright

A PROCESS FOR THE PREPARATION OF OPTICALLY ACTIVE N-BENZYL-3 HYDROXYPYRROLIDINES

The present invention relates to a facile, highly efficient and economical process for the preparation of optically active N-benzyl-3-hydroxypyrrolidine in high yield from a naturally occurring alkaloid vasicine. The natural alkaloid vasicine is used as a precursor of (S)-N-benzyl-3-hydroxypyrrolidine and (R)-N-benzyl-3-hydroxypyrrolidines which can easily be sourced from the medicinal plant Adatoda vasica by the method known in the art and transformed to optical isomers (R) and (S)-N-benzyl-3-hydroxypyrrolidine by the method described in the present invention.