Aluminium lithium hydride → (4-(4-phenylthiazol-2-yl)tetrahydro-2H-pyran-4-yl)methanamine

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Reaction Steps

To a suspension of LiAlH4 (220 mg, 5.9 mmol) in dry THF (10 mL) was added a solution of 4-(4-phenylthiazol-2-yl)tetrahydro-2H-pyran-4-carbonitrile (400 mg, 1.47 mmol) in dry THF (10 mL) at 0° C. The reaction mixture was stirred at room temperature for 1 h and then quenched carefully with water and diluted with EtOAc. The organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography (neutral alumina, eluent 5% MeOH in CHCl3) to afford (4-(4-phenylthiazol-2-yl)tetrahydro-2H-pyran-4-yl)methanamine (150 mg, yield 37%): 1H NMR (400 MHz, CDCl3) δ 7.89-7.91 (m, 2H), 7.48 (s, 1H), 7.33-7.46 (m, 3H), 3.89-3.93 (m, 2H), 3.63-3.69 (m, 2H), 3.03 (s, 2H), 2.30-2.33 (m, 2H), 1.90-1.97 (m, 2H). MS (ESI) m/z: Calculated for C15H18N2OS: 274.11. found: 275.2 (M+H)+.

Provenance & Evidence