77164-20-6

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

• 61248-99-5 (S)-1,2-epoxy-3-(2-methoxyphenyloxy)-propane 
• 75-31-0 isopropylamine 
• 2210-74-4 2-(2-methoxy-phenoxymethyl)-oxirane 
• 719276-44-5 (R)-4-(2-Methoxy-phenoxymethyl)-[1,3,2]dioxathiolane 2-oxide 
• 850427-92-8 (R)-4-(2-Methoxy-phenoxymethyl)-[1,3,2]dioxathiolane 2,2-dioxide 
• 4125-43-3 O-allyl guaiacol 
• 90-05-1 2-methoxy-phenol 
• 61248-76-8 (S)-guaifenesin 
• 18167-91-4 2(2-methoxyphenoxy)ethanale 
• 1415419-09-8 (S)-1-(2-methoxyphenoxy)-3-nitropropan-2-ol 
• 93-14-1 guaifenesin 
• 136167-44-7 3-(2-methoxyphenoxy)propan-1-ol 
• 680185-89-1 3-(2-methoxyphenoxy)propanal 
• 141987-47-5 (R)-1-chloro-3-(2-methoxyphenoxy)-2-propanol 

Relevant academic research and scientific papers

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.

A new catalyst for the asymmetric Henry reaction: Synthesis of β-nitroethanols in high enantiomeric excess

A new chiral tetrahydrosalen ligand has been designed and synthesized from cis-2,5-diaminobicyclo[2.2.2]octane. The complex generated in situ by the interaction of the ligand with (CuOTf)2·C6H 5CH3 was an efficient catalyst for the asymmetric Henry reaction, producing nitroaldol products in high yield and good stereoselectivity. Henry reactions catalyzed by this tetrahydrosalen-Cu(I) complex led to syntheses of β-adrenergic blocking agents (S)-toliprolol, (S)-moprolol, and (S)-propanolol.

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.

Solid state properties and effective resolution procedure for guaifenesin, 3-(2-methoxyphenoxy)-1,2-propanediol

Racemic expectorant guaifenesin, 3-(2-methoxyphenoxy)-1,2-propanediol 2 undergoes spontaneous resolution upon crystallization. This fact is confirmed by thermal analysis (single eutectic V-shape binary melting phase diagram, adequate entropy and free energy characteristics). Racemic 2 could be effectively resolved into (S)- and (R)-2 by a preferential crystallization procedure. Single enantiomer drugs levomoprolol and levotensin were obtained by starting from enantiomeric 2 through the sulfite route.

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.

Jacobsen-type enantioselective hydrolysis of aryl glycidyl ethers. 31P NMR analysis of the enantiomeric composition of oxiranes

The enantioselective partial hydrolysis of a number of racemic aryl glycidyl ethers in the presence of chiral Co(salen)-catalyst was studied. The enantiomeric composition of the isolated (R)-aryl glycidyl ethers was analyzed by 31P NMR using optically active substituted 2-chloro-1,3,2- dioxaphospholanes. A synthesis of β-adrenoblocking agents (S)-toliprolol and (S)-moprolol based on the simultaneously obtained (S)-3-aryloxypropane-1,2- diols was proposed.

Enantioselective ring opening of epoxides with trimethylsilyl azide (TMSN3) in the presence of β-cyclodextrin: An efficient route to 1,2-azido alcohols

The ring opening of epoxides with nucleophiles such as TMSN3 and isopropylamine takes place enantioselectively in the presence of β- cyclodextrin under extremely mild conditions and the azido alcohols and amino alcohols are formed as (S)-isomers. (C) 1999 Published by Elsevier Science Ltd.

Synthesis of novel and enantiomerically pure epoxypropylamine: A divergent route to the chiral β-adrenergic blocking agents

The chiral building block (S)-N-benzyl-N-isopropyl-2,3-epoxypropylamine is obtained by means of chlorohydroxylation of allylamine, followed by Jacobsen's hydrolytic kinetic resolution with water. A concise, divergent five-step synthesis of three β-adrenergic blocking agents in high enantiomeric excess using (S)-N-benzyl-N-isopropyl-2,3-epoxypropylamine as the key intermediate is described.

Enzyme Catalyzed Stereoselective Synthesis of (S)-Propanolamines

Stereoselective synthesis of (S)-propanolamines has been carried out by the ring opening of racemic epoxides with 2-propylamine in presence of lipases and subtilisin.The effect of solvent towards selectivity has also been studied.

STEREOSELECTIVE SYNTHESIS OF (S)-PROPANOL AMINES: LIPASE CATALYZED OPENING OF EPOXIDES WITH 2-PROPYLAMINE

The ring opening of epoxides with 2-propylamine in presence of lipase in organic solvents affords selectively (S)-propanol amines.The effect of solvents towards selectivity has also been examined.