77164-20-6

Basic information

• Product Name: Levomoprolol
• Synonyms: Levomoprolol;(S)-1-(Isopropylamino)-3-(2-methoxyphenoxy)propan-2-ol
• CAS NO: 77164-20-6
• Molecular Formula: C₁₃H₂₁NO₃
• Molecular Weight: 239.313
• Mol File: 77164-20-6.mol
• Article Data: 11

Chemical Properties

• Melting Point: 78-80°
• Boiling Point: 379.2°C at 760 mmHg
• Flash Point: 183.2°C
• Appearance: /
• Density: 1.054g/cm³
• Vapor Pressure: 1.99E-06mmHg at 25°C
• Refractive Index: 1.509
• Storage Temp.: 2-8°C
• CAS DataBase Reference: Levomoprolol(CAS DataBase Reference)
• NIST Chemistry Reference: Levomoprolol(77164-20-6)
• EPA Substance Registry System: Levomoprolol(77164-20-6)

Safety Data

• Hazardous Substances Data: 77164-20-6(Hazardous Substances Data)

Usage

InChI:InChI=1/C13H21NO3/c1-10(2)14-8-11(15)9-17-13-7-5-4-6-12(13)16-3/h4-7,10-11,14-15H,8-9H2,1-3H3/t11-/m0/s1

Upstream product

• 75-31-0 isopropylamine 
• 2210-74-4 2-(2-methoxy-phenoxymethyl)-oxirane 
• 93-14-1 guaifenesin 
• 136167-44-7 3-(2-methoxyphenoxy)propan-1-ol 
• 680185-89-1 3-(2-methoxyphenoxy)propanal 
• 247033-01-8 (S)-N-benzyl-N-isopropyl-2,3-epoxypropylamine 
• 247033-00-7 N-benzyl-N-isopropylallylamine 
• 719276-44-5 (R)-4-(2-Methoxy-phenoxymethyl)-[1,3,2]dioxathiolane 2-oxide 
• 61248-76-8 (S)-guaifenesin 
• 90-05-1 2-methoxy-phenol 
• 4125-43-3 O-allyl guaiacol 
• 850427-92-8 (R)-4-(2-Methoxy-phenoxymethyl)-[1,3,2]dioxathiolane 2,2-dioxide 
• 247033-02-9 (S)-1-(Benzyl-isopropyl-amino)-3-(2-methoxy-phenoxy)-propan-2-ol 
• 61248-99-5 (S)-1,2-epoxy-3-(2-methoxyphenyloxy)-propane 

Relevant articles and documents

Chemoenzymatic Route for the Synthesis of (S)-Moprolol, a Potential β-Blocker

A biocatalytic route for the synthesis of a potential β-blocker, (S)-moprolol is reported here. Enantiopure synthesis of moprolol is mainly dependent on the chiral intermediate, 3-(2-methoxyphenoxy)-propane-1,2-diol. Various commercial lipases were screened for the enantioselective resolution of (RS)-3-(2-methoxyphenoxy)propane-1,2-diol to produce the desired enantiomer. Among them, Aspergillus Niger lipase (ANL) was selected on the basis of both stereo- and regioselectivity. The optimized values of various reaction parameters were determined such as enzyme (15 mg/mL), substrate concentration (10 mM), organic solvent (toluene), reaction temperature (30 °C), and time (18 h).The optimized conditions led to achieving >49% yield with high enantiomeric excess of (S)-3-(2-methoxyphenoxy)propane-1,2-diol. The lipase-mediated catalysis showed regioselective acylation with dual stereoselectivity. Further, the enantiopure intermediate was used for the synthesis of (S)-moprolol, which afforded the desired β-blocker. Chirality 28:313-318, 2016.

Exploration of l-proline-catalyzed α-aminoxylation of aldehyde to (s)-guaifenesin-related drug molecules

An efficient enantioselective synthesis of (S)-guaifenesin with >99% ee using L-proline-catalyzed α-aminoxylation of aldehyde as key step is described and explored for asymmetric syntheses of (S)-moprolol and (R)-methocarbamol.

Asymmetric synthesis of aryloxypropanolamines via OsO4-catalyzed asymmetric dihydroxylation

A simple and effective procedure for the enantioselective synthesis of several β-adrenergic blocking agents incorporating the first asymmetric synthesis of celiprolol, is described. The key steps are (i) sharpless asymmetric dihydroxylation of aryl allyl ethers to introduce chirality into the molecules and (ii) conversion of cyclic sulfates into the corresponding epoxides using a three-step procedure.