p-Toluenesulfonic acid → 5-methoxy-N-(2-(thiophen-2-yl)ethyl)-1,2,3,4-tetrahydronaphthalen-2-amine
Reaktionsgleichung
CCC[N:4]([C@@H:12]1[CH2:17][C:16]2[CH:18]=[CH:19][CH:20]=[C:21]([OH:22])[C:15]=2[CH2:14][CH2:13]1)[CH2:5][CH2:6][C:7]1[S:11][CH:10]=[CH:9][CH:8]=1.Cl.[CH3:24]OC1C=CC=C2C=1CCC(=O)C2.S1C=CC=C1CCN.C1(C)C=CC(S(O)(=O)=O)=CC=1.C([BH3-])#N.[Na+]>>[CH3:24][O:22][C:21]1[CH:20]=[CH:19][CH:18]=[C:16]2[C:15]=1[CH2:14][CH2:13][CH:12]([NH:4][CH2:5][CH2:6][C:7]1[S:11][CH:10]=[CH:9][CH:8]=1)[CH2:17]2Komponenten
Versuchsvorschrift
The preparation of racemic rotigotine hydrochloride is disclosed in U.S. Pat. No. 4,564,628. The process, which is depicted in Scheme 1, comprises reacting 5-methoxy-2-tetralone (Compound I) with β-(2-thienyl)ethylamine in presence of p-toluenesulfonic acid and sodium cyanoborohydride to obtain 1,2,3,4-tetrahydro-5-methoxy-N-[2-(thienyl)-ethyl]-2-naphthaleneamine (Compound II), which is reacted with propionyl chloride in presence of triethylamine to obtain N-(1,2,3,4-tetrahydro-5-methoxy-2-naphthenyl)-N-[2-(2-thienyl)ethyl)]propaneamide (Compound III). This propanamide is reduced with lithium aluminum hydride to obtain 1,2,3,4-tetrahydro-5-methoxy-N-propyl-N-[2-(2-thienyl)ethyl]-2-naphthaleneamine (Compound IV), which is subsequently reacted with boron tribromide, then hydrochloric acid (HCl) to form the racemic rotigotine hydrochloride (Compound V).
Quellen und Nachweise
- ORD-Eintrag
- ord-cf85507b40834ba792908a1f7574baf7
- Quelldatensatz
- uspto-grants-2013_01
- Patentnummer
- US08344165B2
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