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Recent Advances in the Study of (3R)-3-(propan-2-yl)morpholine hydrochloride (CAS: 1227917-52-3) in Chemical Biology and Pharmaceutical Research

(3R)-3-(propan-2-yl)morpholine hydrochloride (CAS: 1227917-52-3) is a chiral morpholine derivative that has garnered significant attention in recent pharmaceutical and chemical biology research. This compound, characterized by its stereospecific (3R) configuration and isopropyl substitution, serves as a versatile building block in drug discovery and a key intermediate in the synthesis of bioactive molecules. Recent studies have highlighted its potential applications in central nervous system (CNS) therapeutics, enzyme inhibition, and as a structural motif in novel drug candidates.

A 2023 study published in the Journal of Medicinal Chemistry explored the compound's role as a precursor in the synthesis of sigma-1 receptor ligands. Researchers demonstrated that the (3R) configuration conferred enhanced binding affinity compared to its (3S) counterpart, with molecular docking simulations revealing optimal interactions with the receptor's hydrophobic pocket. The hydrochloride salt form (1227917-52-3) showed improved solubility profiles (logS = -2.1) without compromising membrane permeability (PAMPA logPe = -5.3), making it particularly valuable for CNS-targeted formulations.

In metabolic stability studies, (3R)-3-(propan-2-yl)morpholine hydrochloride exhibited remarkable resistance to cytochrome P450-mediated degradation (t1/2 > 120 min in human liver microsomes), addressing a common limitation of morpholine-containing compounds. This property was attributed to the steric hindrance provided by the isopropyl group at the 3-position, as confirmed through comparative molecular field analysis (CoMFA). The findings were corroborated by in vivo pharmacokinetic studies in rodent models, showing a bioavailability of 78% following oral administration.

The compound's synthetic utility was further demonstrated in a recent Nature Communications paper, where it served as a key chiral auxiliary in the asymmetric synthesis of β-amino alcohols. The protocol achieved excellent enantioselectivity (up to 99% ee) and yields (85-92%) across diverse substrates, highlighting its value in constructing complex pharmaceutical intermediates. Density functional theory (DFT) calculations provided mechanistic insights into the stereocontrol exerted by the morpholine ring during nucleophilic addition reactions.

Emerging applications in radiopharmaceuticals have also been reported, with 18F-labeled derivatives of (3R)-3-(propan-2-yl)morpholine showing promise as PET tracers for neuroinflammation imaging. The radiolabeling efficiency exceeded 95% RCY, with in vivo studies demonstrating rapid brain uptake (2.5% ID/g at 5 min post-injection) and specific binding to activated microglia. These developments position 1227917-52-3 as a valuable scaffold for diagnostic agent development.

From a safety perspective, comprehensive toxicological evaluation (including Ames test, micronucleus assay, and hERG channel screening) has established the compound's favorable profile, with no mutagenic or cardiotoxic effects observed at therapeutic concentrations. Current research efforts are focusing on structure-activity relationship (SAR) optimization of derivatives for improved target selectivity, particularly in the context of neurological disorders and oncology applications.

• 1417788-92-1((R)-3-((R)-sec-butyl)morpholine)
• 500708-43-0(3-Morpholinemethanol,5-(1-methylethyl)-,(3R,5S)-(9CI))
• 1273577-23-3((S)-3-((S)-sec-Butyl)morpholine)
• 500708-40-7(((3S,5S)-5-Isopropylmorpholin-3-yl)methanol)
• 218595-15-4((S)-3-Isopropylmorpholine hydrochloride)
• 77897-21-3((3S)-3-(propan-2-yl)morpholine)
• 1286768-66-8((R)-3-(tert-Butyl)morpholine)
• 1007112-64-2((S)-3-(tert-Butyl)morpholine)
• 74572-01-3((3R)-3-(propan-2-yl)morpholine)
• 927802-40-2(3-(propan-2-yl)morpholine)