Reaktionsgleichung
CO[CH2:3][NH:4][CH2:5][CH2:6][C@@H:7]([C:9]1[S:10][CH:11]=[CH:12][CH:13]=1)[OH:8].[H-].[Na+].F[C:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][CH:18]=1.CN(C)[CH:29]=[O:30]>>[CH3:3][N:4]([CH2:5][CH2:6][CH:7]([O:8][C:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][CH:18]=1)[C:9]1[S:10][CH:11]=[CH:12][CH:13]=1)[O:30][CH3:29]Komponenten
Reaktionsbedingungen
- Temperatur
- 70 °C
Versuchsvorschrift
10.0 g of (S)-3-methoxymethylamino-1-(2-thienyl)propan-1-ol from example 2 was dissolved in 30 mL of N,N-dimethylformamide at ambient temperature, to which was added sodium hydride (3.9 g, 60%) with vigorous stirring. Then, 9.4 g of 1-fluoronaphthalene was added and the mixture was stirred at 70° C. for 8 hours. Upon completion of naphthalenation, the reaction mixture was quenched with water (90 mL). After extraction with toluene (30 mL×3), the organic layer was combined and concentrated. Subsequently, the crude product was purified by silica gel column chromatography to give objective compound as an amber oil (13.5 g, 82.8%). 1H NMR (400 MHz, CDCl3) δ (ppm)=2.3 (m, 1H), 2.5 (m, 1H), 2.6 (s, 3H), 2.9 (t, 2H), 3.5 (s, 3H), 5.8 (m, 1H), 6.8 (m, 1H), 6.9 (d, 1H), 7.0 (s, 1H), 7.2 (d, 1H), 7.3 (m, 1H), 7.4 (d, 1H) 7.5 (m, 2H), 7.8 (d, 1H), 8.3 (d, 1H).
Aufarbeitung
- customUpon completion of naphthalenation, the reaction mixture was quenched with water (90 mL)
- extractionAfter extraction with toluene (30 mL×3)
- concentrationconcentrated
- customSubsequently, the crude product was purified by silica gel column chromatography
Quellen und Nachweise
- ORD-Eintrag
- ord-530f48ad8dab4d0c88b7cb8110219ae6
- Quelldatensatz
- uspto-grants-2012_04
- Patentnummer
- US08148549B2
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