112835-48-0

Basic information

• Product Name: (+)-N 0437
• Synonyms: (R)-(+)-6-(PROPYL-(2-THIOPHEN-2-YLETHYL)AMINO)TETRALIN-1-OL;(R)-6-[PROPYL-(2-THIOPHEN-2-YL-ETHYL)-AMINO]-5,6,7,8-TETRAHYDRO-NAPHTHALEN-1-OL;1-NAPHTHALENOL, 5,6,7,8-TETRAHYDRO-6-[PROPYL[2-(2-THIENYL)ETHYL]AMINO]-, (6R)-;R-(+)-ROTIGOTINE;ent-Rotigotine;(R)-Rotigotine Hydrochloride
• CAS NO: 112835-48-0
• Molecular Formula: C19H25NOS
• Molecular Weight: 315.47
• Product Categories: Aromatics;Intermediates & Fine Chemicals;Isotope Labelled Compounds;Pharmaceuticals;Sulfur & Selenium Compounds
• Mol File: 112835-48-0.mol
• Article Data: 32

Chemical Properties

• Boiling Point: 470.1±45.0 °C(Predicted)
• Appearance: /
• Density: 1.15±0.1 g/cm3(Predicted)
• Storage Temp.: Refrigerator
• Solubility: Acetone (Slightly), Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• PKA: 10.49±0.40(Predicted)
• CAS DataBase Reference: (+)-N 0437(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-N 0437(112835-48-0)
• EPA Substance Registry System: (+)-N 0437(112835-48-0)

Safety Data

• Hazardous Substances Data: 112835-48-0(Hazardous Substances Data)

Usage

Uses

It is a non-ergot dopamine agonist drug and is indicated for the treatment of Parkinson’s disease.

Upstream product

• 101945-65-7 2-(N-n-propyl-N-2-[2-thienyl]ethylamino)-5-methoxytetralin 
• 1918-77-0 Thiophene-2-acetic acid 
• 165950-84-5 (S)-1,2,3,4-tetrahydro-5-hydroxy-N-propyl-naphthalen-2-ammonium hydrobromide 
• 1222074-06-7 2-(thiophen-2-yl)ethyl 2-nitrobenzene-1-sulfonate 
• 101470-23-9 Desthienyl-Rotigotine 
• 1222074-05-6 (S)-2-(N-n-propyl-N-2-(thien-2-yl)ethylamino)-5-methoxytetraline hydrobromide 
• 1229620-82-9 (S)-6-(propyl(2-(thiophen-2-yl)ethyl)amino)-5,6,7,8-tetrahydronaphthalen-1-yl acetate hydrochloride 
• 1231158-76-1 (S)-6-(propyl(2-(thiophen-2-yl)ethyl)amino)-5,6,7,8-tetrahydronaphthalen-1-yl acetate hydrobromide 
• 1352917-69-1 (S)-N-(methoxycarbonyl)-N-propyl-5-methoxy-2-aminotetralin 
• 40412-06-4 2-(2-thienyl)ethyl tosylate 
• 1352917-62-4 N-(methoxycarbonyl)-N-propyl-5-methoxy-2-aminotetralin 
• 191339-42-1 2-(2-thiophenylethyl) 4-nitro-benzene sulfonate 
• 32940-15-1 5-methoxy-2-tetralone 
• 1374308-75-4 C₁₄H₁₉NO 

Downstream Products

• 102120-99-0 (-)-5-hydroxy-2-[N-n-propyl-2-(2-thienyl)ethylamino]tetralin hydrochloride 
• 1229620-82-9 (S)-6-(propyl(2-(thiophen-2-yl)ethyl)amino)-5,6,7,8-tetrahydronaphthalen-1-yl acetate hydrochloride 
• 1424879-63-9 rotigotine-2-azidopropionate 
• 1424879-55-9 rotigotine-3-azidopropionate 
• 1424879-51-5 rotigotine-2-azidoacetate 

Relevant articles and documents

Preparation method of rotigotine

The invention relates to the technical field of medicine preparation, and discloses a preparation method of rotigotine, which comprises the following steps: by taking 5-methoxy-2-tetralone as an initial raw material, reacting with R-alpha-methylbenzylamine, performing debenzylation reduction and S-mandelic acid chiral resolution, then reacting with a propionyl chloride reagent to generate an amide compound, and then reducing by a sodium borohydride reagent to obtain the rotigotine; and finally, reacting with 2-(thiophene-2-yl) 2-nitric acid benzene sulfonic acid ethyl ester to obtain the rotigotine. The preparation process route is as follows: the rotigotine is mild in preparation condition, simple and convenient to operate, relatively high in yield of key intermediates, high in optical purity and easy for industrial large-scale production, and has a very good application prospect.

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.

Enantioselective Synthesis of β-Aminotetralins via Chiral Phosphoric Acid-catalyzed Reductive Amination of β-Tetralones

A new protocol for the synthesis of chiral β-aminotetralins has been developed via chiral phosphoric acid-catalyzed asymmetric reductive amination of β-tetralones using a Hantzsch ester as an organic hydride donor. Various chiral β-aminotetralins were obtained in good yields with good to high enantioselectivities. Furthermore, the utility of our new protocol was successfully demonstrated in the enantioselective synthesis of rotigotine. (Figure presented.).