101403-24-1

Basic information

• Product Name: (S)-1,2,3,4-tetrahydro-5-methoxy-N-propyl-2-Naphthalenamine(Rotigotine)
• Synonyms: (S)-1,2,3,4-tetrahydro-5-methoxy-N-propyl-2-Naphthalenamine(Rotigotine);(S)-1,2,3,4-Tetrahydro-5-methoxy-N-propyl-2-naphthalenamine;Rotigotine InterMediate;(S)-5-Methoxy-N-propyl-1,2,3,4-tetrahydronaphthalen-2-aMine;2-NaphthalenaMine, 1,2,3,4-tetrahydro-5-Methoxy-N-propyl-, (S)-
• CAS NO: 101403-24-1
• Molecular Formula: C₁₄H₂₁NO
• Molecular Weight: 219.32
• Product Categories: APIs Intermediate
• Mol File: 101403-24-1.mol
• Article Data: 16

Chemical Properties

• Boiling Point: 346.117 °C at 760 mmHg
• Flash Point: 143.285 °C
• Appearance: /
• Density: 1.014 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.533
• PKA: 10.26±0.20(Predicted)
• CAS DataBase Reference: (S)-1,2,3,4-tetrahydro-5-methoxy-N-propyl-2-Naphthalenamine(Rotigotine)(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-1,2,3,4-tetrahydro-5-methoxy-N-propyl-2-Naphthalenamine(Rotigotine)(101403-24-1)
• EPA Substance Registry System: (S)-1,2,3,4-tetrahydro-5-methoxy-N-propyl-2-Naphthalenamine(Rotigotine)(101403-24-1)

Safety Data

• Hazardous Substances Data: 101403-24-1(Hazardous Substances Data)

Usage

General Description

Rotigotine, also known by its brand name Neupro, is a chemical compound with the formula (S)-1,2,3,4-tetrahydro-5-methoxy-N-propyl-2-Naphthalenamine. It is a dopamine agonist that works by stimulating dopamine receptors in the brain, which helps to regulate motor control and mood. In medicine, it is used as a transdermal patch to treat Parkinson's disease and restless legs syndrome. It is also being investigated for its potential in treating other conditions such as depression and attention deficit hyperactivity disorder (ADHD). Rotigotine is available by prescription and should be used under the guidance of a healthcare professional. Common side effects include dizziness, nausea, and skin irritation at the application site.

InChI:InChI=1/C14H21NO/c1-3-9-15-12-7-8-13-11(10-12)5-4-6-14(13)16-2/h4-6,12,15H,3,7-10H2,1-2H3/t12-/m0/s1

Upstream product

• 3904-24-3 (5-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)propylamine hydrochloride 
• 32940-15-1 5-methoxy-2-tetralone 
• 244239-68-7 (R)-N-(5-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)propionamide 
• 1374308-75-4 C₁₄H₁₉NO 
• 4018-91-1 2-Amino-5-methoxy-1,2,3,4-tetrahydronaphthalene 
• 105086-92-8 (S)-5-methoxy-2-amino-1,2,3,4-tetrahydronaphthalene 
• 107-10-8 propylamine 
• 58349-15-8 (S)-5-methoxy-1,2,3,4-tetrahydronaphthalen-2-amine hydrochloride 
• 244239-67-6 (S)-N-(5-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)propionamide 
• 78598-91-1 2-(N-propylamino)-5-methoxytetraline 
• 101403-23-0 (-)-(2S)-2-(N-benzyl-N-n-propylamino)-5-methoxytetralin 
• 58349-23-8 (S)-(-)-2-(N-benzylamino)-5-methoxytetralin 
• 802294-64-0 propionic acid 

Downstream Products

• 136247-11-5 N-((S)-5-Methoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-2-(4-nitro-phenyl)-N-propyl-acetamide 
• 165950-84-5 (S)-1,2,3,4-tetrahydro-5-hydroxy-N-propyl-naphthalen-2-ammonium hydrobromide 
• 93601-86-6 (S)-(-)-(5-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)propylamine hydrochloride 
• 1148154-91-9 (2S)-5-methoxy-N-propyl-N-(2'-(thien-2-yl)ethyl)tetralin-2-amine 
• 78598-91-1 2-(N-propylamino)-5-methoxytetraline 
• 1563175-00-7 (S)-5-methoxy-N-(2-(4-(3′-methoxybiphenyl-4-yl)piperazin-1-yl)ethyl)-N-propyl-1,2,3,4-tetrahydronaphthalen-2-amine 
• 125572-93-2 rotigotine hydrochloride 
• 99755-59-6 rotigotine 
• 136316-06-8 (S)-(-)-2--5-methoxytetralin 
• 129388-80-3 (S)-(-)-2--5-hydroxytetralin 
• 101470-23-9 Desthienyl-Rotigotine 

Relevant articles and documents

New catalytic route for the synthesis of an optically active tetralone-derived amine for rotigotine

Rotigotine is a launched drug for the treatment of Parkinson's disease and restless legs syndrome. The key steps of an alternative route for the synthesis of rotigotine have been demonstrated. Formation of a prochiral enamide, asymmetric hydrogenation of the enamide with high enantioselectivity, and reduction of the resulting amide to an amine have been proved to work successfully. The best conditions screened to date for the asymmetric hydrogenation of enamide 9 to amide 10 were with [(RuCl((R)-T-BINAP))2(μ-Cl)3][NH2Me2] at 25 bar H2 and 30 °C (500:1 S/C ratio, 99% conversion, 91% ee S). Reduction of amide 10 to amine 5 was best achieved with Red-Al giving 95% conversion.

Synthesis of Pharmaceutically Relevant 2-Aminotetralin and 3-Aminochroman Derivatives via Enzymatic Reductive Amination

2-Aminotetralin and 3-aminochroman derivatives are key structural motifs present in a wide range of pharmaceutically important molecules. Herein, we report an effective biocatalytic approach towards these molecules through the enantioselective reductive coupling of 2-tetralones and 3-chromanones with a diverse range of primary amine partners. Metagenomic imine reductases (IREDs) were employed as the biocatalysts, obtaining high yields and enantiocomplementary selectivity for >15 examples at preparative scale, including the precursors to Ebalzotan, Robalzotan, Alnespirone and 5-OH-DPAT. We also present a convergent chemo-enzymatic total synthesis of the Parkinson's disease therapy Rotigotine in 63 % overall yield and 92 % ee.

Preparation method for rotigotine

The invention discloses a preparation method for rotigotine. The preparation method includes the following steps: S1. performing an amination reduction reaction on a 5-methoxy-2-tetralone solution, tert-butanesulfinamide, a catalyst, and sodium borohydride to obtain a substance A; S2. performing an alkylation reaction on a solution of the substance A, bromopropane, and a basic catalyst to obtain asubstance B; S3. reacting the substance B with a hydrochloric acid methanol solution to obtain a substance C; S4. performing a reaction on the substance C, 2-(2-bromoethyl)thiophene, potassium carbonate, and N,N-dimethylformamide to obtain a substance D; and S5. reacting acetic acid with hydrogen bromide to obtain the rotigotine. The preparation method is simple in operation, is high in yield, ismild in reaction condition, is green and environmentally friendly, is high in purity of the prepared rotigotine, and is suitable for large-scale industrial production.