Water → 8-{5-[4-(Trifluoromethyl)phenyl]oxazol-2-ylamino}-1,2,3,4-tetrahydronaphthalen-2-ol

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Reaktionsgleichung

[F:1][C:2]([F:27])([F:26])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:13][C:12]([NH:14][C:15]3[CH:16]=[CH:17][CH:18]=[C:19]4[C:24]=3[CH2:23][C:22](=[O:25])[CH2:21][CH2:20]4)=[N:11][CH:10]=2)=[CH:5][CH:4]=1.[BH4-].[Na+].O>C(O)C>[F:27][C:2]([F:1])([F:26])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:13][C:12]([NH:14][C:15]3[CH:16]=[CH:17][CH:18]=[C:19]4[C:24]=3[CH2:23][CH:22]([OH:25])[CH2:21][CH2:20]4)=[N:11][CH:10]=2)=[CH:5][CH:4]=1

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

The product of Example 1I (60 mg, 0.161 mmol) in ethanol (6 mL) was treated at 0° C. with NaBH4 (7 mg, 0.184 mmol). The reaction was stirred at 0° C. for 1 hour and was then poured into H2O and extracted with ethyl acetate. The extracts were dried over Na2SO4, and concentrated in vacuo. The residue was chromatographed on silica gel eluting with 70%-85% ethyl acetate-hexane to afford the title compound as a tan solid (34 mg, 56%). 1H NMR (DMSO-d6) δ 9.33 (s, 1H), 7.78 (m, 4H), 7.62 (s, 1H), 7.55 (d, 1H, J=7.4 Hz), 7.11 (m, 1H), 6.88 (d, 1H, J=7.2 Hz), 4.83 (d, 1H, J=4.1 Hz), 3.92 (m, 1H), 2.69-2.98 (m, 4H), 1.86 (m, 1H), 1.62 (m, 1H); MS (ESI+) m/z 375 (M+H).

Aufarbeitung

extractionextracted with ethyl acetate
dry with materialThe extracts were dried over Na2SO4
concentrationconcentrated in vacuo
customThe residue was chromatographed on silica gel eluting with 70%-85% ethyl acetate-hexane

Quellen und Nachweise

ORD-Eintrag: ord-8bf866afe58340a190e1428e2f932e2c
Quelldatensatz: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07902236B2

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