Aluminium lithium hydride → HCID 58724153, compound

Participants

Reaction Steps

Methyl 2-(1-(naphthalen-1-ylsulfonyl)piperidin-4-yl)benzoate (80 mg, 0.02 mmol) was dissolved in 1 mL of anhydrous THF under nitrogen protection. 0.4 mL of LiAlH4 (1.0M solution in THF) was added to the solution through a syringe at −78° C. After 30 minutes, the reaction mixture was quenched with MeOH, evaporated to dryness, and extracted with EtOAc and 0.1 N tartaric acid solution in water. The organic layer was then dried over Na2SO4, and the solvent was removed. The title compound was obtained in 60% yield after purification using preparative HPLC. 1H NMR (400 MHz, DMSO-D6) δ ppm 1.58 (dd, J=12.38, 3.54 Hz, 2 H) 1.67-1.74 (m, 2 H) 2.52-2.61 (m, 2 H) 2.73-2.81 (m, 2 H) 3.88 (d, J=12.13 Hz, 2 H) 4.42 (d, J=3.79 Hz, 2 H) 4.96 (s, 1 H) 7.08-7.19 (m, 3 H) 7.24-7.29 (m, 1 H) 7.66-7.78 (m, 4 H) 8.13 (d, J=8.84 Hz, 1H) 8.17 (d, J=7.33 Hz, 1 H) 8.31 (d, J=8.08 Hz, 1 H) 8.75 (d, J=8.59 Hz, 1 H); ESI-MS: m/z 382.1 (M+H)+.

Provenance & Evidence