Reaktionsgleichung
[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][CH:6]=[CH:5][C:4]=1[CH:11]1SCCCS1.[CH:17]1([CH:23]=[CH:24][C:25](OCC)=[O:26])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1.[OH-].[Na+]>[Ni]>[CH:17]1([CH:23]2[CH2:11][C:4]3[C:5](=[CH:6][CH:7]=[C:8]([O:9][CH3:10])[C:3]=3[O:2][CH3:1])[C:25](=[O:26])[CH2:24]2)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
2-(2',3'-Dimethoxyphenyl)-1,3-dithiane, from Step 1 of Example 1, Method B, and ethyl 3-cyclohexylpropenoate, from Step 1 of this Example, were condensed as described in Step 2 of Example 1, Method B. The adduct was treated with Raney nickel and sodium hydroxide to give the corresponding acid. The acid was cyclized with polyphosphoric acid as described in Step 6 of Example 1, Method A, to give 3-cyclohexyl-5,6-dimethoxy-1,2,3,4-tetrahydronaphthalen-1-one. This ketone was treated with trimethylsilylcyanide in the presence of aluminum chloride and reduced with lithium aluminum hydride as described in Step 1 of Example 2 to give 1-aminomethyl-5,6-dimethoxy-1-hydroxy-3-cyclohexyl-1,2,3,4-tetrahydronaphthalene. The hydroxy group was eliminated by treatment with anhydrous hydrogen chloride in isopropyl alcohol as described in Step 2 of Example 2 to give 1-aminomethyl-3-cyclohexyl-5,6-dimethoxy-3,4-dihydronaphthalene hydrochloride, m.p. 178°-179° C.; 1H NMR (d6 -DMSO) δ: 1.0-1.4 (m, 7H), 1.5-1.9 (m, 6H), 2.0-2.2 (m, 1H), 2.5 (dd, 1H), 2.7 (dd, 1H), 3.6 (s, 3H), 3.81 (s, 3H), 5.8 (d, 1H), 6.6 (m, 2H).
Aufarbeitung
- customcondensed
- customto give the corresponding acid
Quellen und Nachweise
- ORD-Eintrag
- ord-6b5f61e98b8642358d4280c1436b3ac3
- Quelldatensatz
- uspto-grants-1997_01
- Patentnummer
- US05591884
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