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ChemicalBook CAS DataBase List ROTIGOTINE
99755-59-6

ROTIGOTINE synthesis

11synthesis methods
Rotigotine is a non-selective dopamine receptor agonist with preference for D3 receptors over D2 and D1. As such, it is an effective anti-Parkinsonian agent. Racemic rotigotine is about 50 times as potent as quinpirole, the gold standard D2 agonist.
Synthetic Routes
  • ROUTE 1

    • 202112070682610112.jpg

    Webster, Robert; Boyer, Alistair; Fleming, Matthew J.; Lautens, Mark. Practical Asymmetric Synthesis of Bioactive Aminotetralins from a Racemic Precursor Using a Regiodivergent Resolution. Organic Letters. Volume 12. Issue 23. Pages 5418-5421. 2010.

  • ROUTE 2

    • 202112074253795201.jpg

    Khunt, Mayur Devjibhai; Varma, Shrikant; Patil, Nilesh Sudhir; Pagire, Haushabhau Shivaji; Pradhan, Nitin Sharadchandra. Process for preparation of highly pure rotigotine and pharmaceutically acceptable salts thereof. Assignee Actavis Group PTC Ehf, Iceland. WO 2010073124. (2010).

  • ROUTE 3

    • 202112077855834566.jpg

    Lu, Jun; Zhang, Yanfei; Yang, Jin; Mao, Dongyan; Shen, Zongxuan. A preparation method of rotigotine and its derivatives. Assignee Suzhou Chireach Biomedical Technology Co., Ltd., Peop. Rep. China. CN 101717392. (2010).

  • ROUTE 4

    • 202112070822691254.jpg

    Park, Do Young; Kim, Kyung-Hee; Cheon, Cheol-Hong. Enantioselective Synthesis of β-Aminotetralins via Chiral Phosphoric Acid-catalyzed Reductive Amination of β-Tetralones. Advanced Synthesis & Catalysis. Volume 360. Issue 3. Pages 462-467. 2018.

  • ROUTE 5

    • 202112071043909090.jpg

    Cobley, Christopher J.; Evans, George; Fanjul, Tamara; Simmonds, Shaun; Woods, Amy. New catalytic route for the synthesis of an optically active tetralone-derived amine for rotigotine. Tetrahedron Letters. Volume 57. Issue 9. Pages 986-989. 2016.

  • ROUTE 6

    • 202112079591021477.jpg

    He, Xungui; Guo, Jianping; Wang, Yanling; Tang, Wensheng; Zhang, Xingzhong; Wang, Xuezhang; Wang, Yuan. A process for preparing rotigotine and its pharmaceutically acceptable salts. Assignee 2Y-Chem, Ltd., Peop. Rep. China. WO 2011026318. (2011).

  • ROUTE 7

    • 202112074165429905.jpg

    Pomares, Marta; Marquillas, Francisco. Process for the preparation of (6S)-(-)-5,6,7,8-tetrahydro-6-[propyl-(2-thienyl)ethyl]amino-1-naphthol (rotigotine) using improved alkylation and hydrolysis steps. Assignee Interquim, S.A., Spain. WO 2010066755. (2010).

  • ROUTE 8

    • 202112079866105548.jpg

    Kandula, Mahesh. Compositions and methods for treatment of neurologic diseases. WO 2013168033. (2013).

  • ROUTE 9

    • 202112076663383830.jpg

    Wang, Keliu; Wang, Meihai. Process for preparation of rotigotine. Assignee Shandong Lubei Pharmaceutical Limited, Peop. Rep. China. CN 103058985. (2013).

  • ROUTE 10

    • 202112073541140596.jpg

    Irudayaraj, Victor Paul Raj; Subramani, Senthilkumar; Govindaraj, Vedhachalam; Jayavelu, Jeyakanthan; Jayaraman, Boopathy; Ray, Uttam Kumar; Vittal, Tangirala. Novel process for preparation of rotigotine and intermediates thereof from ( S)-1,2,3,4-tetrahydro-5-methoxy-N-propyl-2-naphthalenamine hydrochloride and 2-thiopheneacetyl chloride via demethylation of (2S)-N-(5-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)-N-propyl-2-(thien-2-yl)ethanamide with aluminum chloride. Assignee Solara Active Pharma Sciences Limited, India. US 20190248758. (2019).

202112070682610112.jpg

Webster, Robert; Boyer, Alistair; Fleming, Matthew J.; Lautens, Mark. Practical Asymmetric Synthesis of Bioactive Aminotetralins from a Racemic Precursor Using a Regiodivergent Resolution. Organic Letters. Volume 12. Issue 23. Pages 5418-5421. 2010.

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Yield:99755-59-6 98%

Reaction Conditions:

with sodium carbonate in dichloromethane;water

Steps:

13
Example 13 Dissociation of Rotigotine hydrochloride To a 10L four-necked reaction flask equipped with a mechanical agitator and a constant pressure dropping funnel, the above prepared 363g purified rotigotine hydrochloride and dichloromethane (5475mL) were added, and neutralized by dropwise addition of 5% aqueous sodium carbonate solution. The organic phase was separated out and washed with water once and concentrated to dryness to give 320g oil. Hexane (600mL) was added to the residue to precipitate a solid, which was filtered and dried to give rotigotine solid. Chemical Purity: 99.82%, Optical Purity: 100%, Yield: 98%. 1H-NMR(400MHz, CDCl3):δ 7.12(m, 1H, aromatic), 7.0(m, 1H, aromatic), 6.9(m, 1H, aromatic), 6.8(m, 1H, aromatic), 6.7(m, 1H, aromatic), 6.6(m, 1H, aromatic), 4.9(broad double, 1H, -OH), 2.8(m, 8H, -CH2-, -CH-), 2.6 (m, 3H, -CH2-), 2.10(m, 1H, -CH2-), 1.5(m, 3H, -CH2-), 0.9 (t, 3H, -CH3).

References:

2y-Chem, Ltd. EP2476676, 2012, A1 Location in patent:Page/Page column 9

FullText

1148154-91-9 Synthesis
(S)-5-Methoxy-N-propyl-N-(2-(thiophen-2-yl)ethyl)-1,2,3,4-tetrahydronaphthalen-2-aMine

1148154-91-9
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