Aluminium lithium hydride → HCID 178432775, compound

Participants

Reaction Conditions

Reaction Steps

Trans-4-[(5-Chloro-2-methyl-pyridine-3-carbonyl)-amino]-cyclohexanecarboxylic acid methyl ester (step 1) (2.20 g, 7.08 mmol) was placed in a flask with dry THF (100 ml). This was cooled to 0° C. and lithium aluminum hydride (0.537 g, 14.16 mmol) was added. The reaction mixture was stirred at RT for 2 hours and then quenched with water (0.5 ml), 2M NaOH (0.5 ml) and then water again (1.5 ml). The solids were filtered off through Celite® (filter material) and the filtrate was partitioned between EtOAc and water. The organic phase was washed with water and brine, dried over MgSO4, filtered and the solvent was removed in vacuo to afford the title product which was used in the next step without further purification. 1H NMR (400 MHz, DMSO-d6) δ 8.53 (1H, d), 8.38*1H, d), 7.79 (1H, d), 4.40 (1H, t), 3.66 (1H, m), 3.21 (2H, t), 2.47 (3H, s), 1.92 (2H, m), 1.78 (2H, m), 1.31 (1H, m), 1.22 (2H, m), 0.98 (2H, m). [M+H]+283.30.

Provenance & Evidence