Sodium hydride → HCID 58993646, compound

Participants

Reaction Conditions

Reaction Steps

Methyl 3-bromo-5-(bromomethyl)benzoate (2.1 g, 6.81 mmol) and tert-butyl 4-(hydroxymethyl)-4-phenylpiperidine-1-carboxylate (1.8 g, 6.2 mmol) were combined in dimethylformamide (21 mL) and cooled to 0° C. The reaction was treated with sodium hydride (298 mg, 12.4 mmol), stirred at 0° C. for 1 h, and at room temperature for 30 min. The reaction was cooled to 0° C. and treated lithium hydroxide monohydrate (0.54 g, 13.6 mmol). The solution was stirred at room temperature for 16 h and the solvents evaporated. The resultant residue was diluted with water (10 mL) and the pH adjusted to ca. 1 with 1 N hydrochloric acid. The resultant white suspension was stored at 4° C. overnight and the product was collected by filtration, washed with a small amount of water, and dried in vacuo for several hours to afford 2.4 g (70%) as a white powder. LC/MS: tR=3.33 min, 506.20 (MH)+. (Phenomenex C18 4.6×50 mm, 10% MeOH/90% H2O/0.1% TFA→90% MeOH/10% H2O/0.1% TFA, Gradient time=4 min., Flow rate=4 mL/min.).

Provenance & Evidence