127931-15-1

Basic information

• Product Name: R-(+)-Naftopidil
• Synonyms: 1-Piperazineethanol, 4-(2-methoxyphenyl)-a-[(1-naphthalenyloxy)methyl]-, (R)- (9CI);R-(+)-Naftopidil
• CAS NO: 127931-15-1
• Molecular Formula: C₂₄H₂₈N₂O₃
• Molecular Weight: 0
• Mol File: 127931-15-1.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: R-(+)-Naftopidil(CAS DataBase Reference)
• NIST Chemistry Reference: R-(+)-Naftopidil(127931-15-1)
• EPA Substance Registry System: R-(+)-Naftopidil(127931-15-1)

Safety Data

• Hazardous Substances Data: 127931-15-1(Hazardous Substances Data)

Upstream product

• 57149-07-2 naftopidil 
• 90-15-3 α-naphthol 
• 90-04-0 2-methoxy-phenylamine 
• 51594-55-9 (R)-(-)-epichlorohydrin 
• 35386-24-4 1-(2-Methoxyphenyl)piperazine 
• 67843-74-7 (S)-epichlorohydrin 
• 61248-78-0 (R)-3-(1-naphthyloxy)-1,2-propanediol 
• 766-51-8 2-Chloroanisole 
• 2461-42-9 3-(1-naphthyloxy)-1,2-epoxypropane 

Relevant articles and documents

Hydrolytic kinetic resolution of α-naphthyl glycidyl ether: A practical access to highly enantioselective β-adrenergic blocking agents

Kinetic resolution of (±)-naphthyl glycidyl ether using 0.5 mol% (R,R)-salen Co(III)OAc and water (0.55 equiv) provided enantiomerically pure naphthyl glycidyl ether and 1-naphthylglycerol derivatives with high enantiomeric excess. Application of this approach to highly enantioenriched (S)-naftopidil and (S)-propranolol is described. Georg Thieme Verlag Stuttgart.

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.).

Asymmetric synthesis of propranolol, naftopidil and (R)-monobutyrin using a glycerol desymmetrization strategy

Herein, an approach for desymmetrization of glycerol by using a readily available camphorsulfonamide as a starting material is described. The strategy for asymmetric synthesis of (R)/(S)-propranolol, (R)/(S)-naftopidil and (R)-monobutyrin with spiroketal formation by desymmetrization was employed and Mitsunobu reaction was used for epoxide and ether formation. Steglich esterification and CAN (cerium ammonium nitrate) mediated ketal deprotection, were key steps in the synthesis. Regioselective ring opening of epoxide gave desired molecule with good overall yield and optical purity.