Water → 6-(4-Morpholinyl)-2-pyridinemethanol
Reaktionsgleichung
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Si]([O:26][CH2:27][C:28]1[N:33]=[C:32]([N:34]2[CH2:39][CH2:38][O:37][CH2:36][CH2:35]2)[CH:31]=[CH:30][CH:29]=1)(C(C)(C)C)(C)C.O>C1COCC1>[N:34]1([C:32]2[N:33]=[C:28]([CH2:27][OH:26])[CH:29]=[CH:30][CH:31]=2)[CH2:35][CH2:36][O:37][CH2:38][CH2:39]1Komponenten
Versuchsvorschrift
A solution of tetrabutylammonium fluoride (1.44 mmol) in THF (1.0 M, 1.44 ml) was added to a stirred solution of 4-[6-(tert-butyldimethylsilanyloxymethyl)-pyridin-2-yl]morpholine (370 mg, 1.2 mmol) in THF (10 ml) at room temperature under N2 and the reaction mixture was stirred at room temperature for 1 h. H2O (30 ml) was added and the organic were extracted with EtOAc (150 ml), then washed with brine (50 ml), dried and concentrated under reduced. The mixture was purified by column chromatography on silica using 100% Et2O as eluent to yield the desired hydroxymethylpyridine (192 mg, 82%). 1H NMR (360 MHz, CDCl3) δ 7.49 (1H, dd, J=8.4, 7.4 Hz), 6.57 (1H, d, J=7.4 Hz), 6.51 (1H, d, J=8.4 Hz), 4.62 (2H, s), 3.83 (4H, t, J=4.9 Hz), 3.50 (4H, t, J=4.9 Hz).
Aufarbeitung
- extractionthe organic were extracted with EtOAc (150 ml)
- washwashed with brine (50 ml)
- customdried
- concentrationconcentrated
- customThe mixture was purified by column chromatography on silica using 100% Et2O as eluent
Quellen und Nachweise
- ORD-Eintrag
- ord-7dbea7aeb97049f29426dc30322ce781
- Quelldatensatz
- uspto-grants-2005_05
- Patentnummer
- US06900209B2
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