Triethylamine hydrochloride → HCID 11804772, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of potassium (±)-threo-5-(4-fluorophenyl)-4,5-dihydrooxazole-4-carboxylate, ANP 20162 (500 mg, 2.02 mmol), and triethylamine hydrochloride (278.3 mg, 2.02 mmol) in 50 mL of anhydrous CHCl3 at 4° C., was added HOBT (300.5 mg, 2.22 mmol) and EDCI (426.3 mg, 2.22 mmol). The reaction mixture was stirred at 4° C. for 10 min under nitrogen and 4-methylpiperidine (477.5 μL, 4.04 mmol) was added dropwise. The reaction mixture was stirred at 4° C. to RT for 15 h under nitrogen. The solvent was evaporated and the obtained residue was partitioned between EtOAc (150 mL) and 1N NaOH (50 mL). The organic layer was washed with brine (20 mL), dried over MgSO4, filtered and evaporated to give (±)-trans-5-(4-fluorophenyl)-4,5-dihydrooxazol-4-yl)(4-methylpiperidin-1-yl)methanone, LPO 26074 as a red oil (590 mg, 100% crude yield).

Provenance & Evidence