Aluminium lithium hydride → HCID 43314999, compound

Participants

Reaction Steps

To a solution of tert-butyl 1-(3-(trifluoromethyl)benzyl)piperidin-4-ylcarbamate (0.358 g, 1 mmol; Example 41A) in tetrahydrofuran (40 mL) was added LiAlH4 (0.056 g, 1.5 mmol) and the resultant mixture was heated to reflux for 16 hours. Then the reaction mixture was cooled in an ice bath and Na2SO4.10H2O (0.1 g) was added. The mixture was stirred for 1 hour at room temperature, and then the inorganic salts were removed by filtration. The filtrate was evaporated, and the obtained residue was chromatographed on silica gel eluting with 5-10% methanol/dichloromethane to yield the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 7.58 (s, 1H), 7.51 (m, 2H), 7.42 (m, 1H), 5.36 (Bs, 1H), 3.54 (s, 2H), 2.82 (m, 2H), 2.43 (s, 3H), 2.37 (m, 1H), 2.07 (m, 2H), 1.87 (d, J=12.55 Hz, 2H), 1.38 (m, 2H); MS (DCI+) m/z 273 (M+H)+.

Provenance & Evidence