61249-00-1

Usage

Uses

Used in Pharmaceutical Industry:
Oxirane, ((1-naphthalenyloxy)methyl)-, (S)is used as a key intermediate in the synthesis of Naftopidil (N213500) enantiomers. Naftopidil is a selective α1A-adrenergic receptor antagonist used in the treatment of benign prostatic hyperplasia (BPH) and other urological conditions. The (S)-enantiomer of Naftopidil is known to have a higher affinity for the α1A-adrenergic receptor, making it a more effective therapeutic agent.
The use of Oxirane, ((1-naphthalenyloxy)methyl)-, (S)in the preparation of Naftopidil enantiomers allows for the production of a more targeted and effective medication, improving patient outcomes and providing a more precise treatment option for urological conditions.

Upstream product

• 2461-42-9 3-(1-naphthyloxy)-1,2-epoxypropane 
• 90-15-3 α-naphthol 
• 62-53-3 aniline 

Downstream Products

• 121637-13-6 (S)-6-[(S)-2-Hydroxy-3-(naphthalen-1-yloxy)-propylamino]-heptanoic acid p-tolylamide 
• 121637-14-7 (R)-6-[(S)-2-Hydroxy-3-(naphthalen-1-yloxy)-propylamino]-heptanoic acid p-tolylamide 
• 125452-58-6 (S)-6-[(S)-2-Hydroxy-3-(naphthalen-1-yloxy)-propylamino]-heptanoic acid (4-trifluoromethyl-phenyl)-amide 
• 125452-56-4 (R)-6-[(S)-2-Hydroxy-3-(naphthalen-1-yloxy)-propylamino]-heptanoic acid (4-trifluoromethyl-phenyl)-amide 
• 1335302-64-1 (S)-benzyl 4-(2-hydroxy-3-(naphthylen-1-yloxy)propylamino)butylcarbamate 
• 1335302-63-0 (S)-benzyl 2-(2-hydroxy-3-(naphthylen-1-yloxy)propylamino)ethylcarbamate 
• 1335302-65-2 (S)-benzyl 8-(2-hydroxy-3-(naphthylen-1-yloxy)propylamino)octylcarbamate 
• 1335302-72-1 (S)-benzyl 2-(2-(2-(2-hydroxy-3-(naphthylen-1-yloxy)propylamino)ethoxy)ethoxy)ethylcarbamate 
• 23357-46-2 (R)-1,2,3,4-Tetrahydro-1-naphthylamine 
• 127931-16-2 (S)-(-)-1-<4-(2-Methoxyphenyl)-1-piperazinyl>-3-(1-naphthyloxy)-2-propanol 
• 88547-38-0 (-)-Desisopropylpropranolol 
• 4199-09-1 (S)-1-isopropylamino-3-(1-naphthyloxy)-2-propanol 
• 4199-10-4 (S)-(-)-propanolol hydrochloride 

Relevant academic research and scientific papers

Asymmetric Hydrolytic and Aminolytic Kinetic Resolution of Racemic Epoxides using Recyclable Macrocyclic Chiral Cobalt(III) Salen Complexes

New chiral macrocyclic cobalt(III) salen complexes were synthesized and used as catalyst for the asymmetric kinetic resolution (AKR) of terminal epoxides and glycidyl ethers with aromatic/aliphatic amines and water as nucleophiles. This is the first occasion where a Co(III) salen complex demonstrated its ability to catalyze AKR as well as hydrolytic kinetic resolution (HKR) reactions. Excellent enantiomeric excesses of the epoxides, the corresponding amino alcohols and diols (upto 99%) with quantitative yields were achieved by using the chiral Co(III) salen complexes in dichloromethane at room temperature. This protocol was further extended for the synthesis of two important drug molecules, i.e., (S)-propranolol and (R)-naftopidil. The catalytic system was also explored for the synthesis of chirally pure diols and chiral cyclic carbonates using carbon dioxide as a greener renewable C1 source. The catalyst was recycled for upto 5 catalytic cycles with retention of enantioselectivity. (Figure presented.).

An unusual (R)-selective epoxide hydrolase with high activity for facile preparation of enantiopure glycidyl ethers

A novel epoxide hydrolase (BMEH) with unusual (R)-enantioselectivity and very high activity was cloned from Bacillus megaterium ECU1001. Highest enantioselectivities (E>200) were achieved in the bioresolution of ortho-substituted phenyl glycidyl ethers and para-nitrostyrene oxide. Worthy of note is that the substrate structure remarkably affected the enantioselectivities of the enzyme, as a reversed (S)-enantiopreference was unexpectedly observed for the ortho-nitrophenyl glycidyl ether. As a proof-of-concept, five enantiopure epoxides (>99% ee) were obtained in high yields, and a gram-scale preparation of (S)-ortho-methylphenyl glycidyl ether was then successfully performed within a few hours, indicating that BMEH is an attractive biocatalyst for the efficient preparation of optically active epoxides. Copyright