Triethylamine hydrochloride → HCID 11804772, compound

Temperature

4 °C

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).

1. stirringThe reaction mixture was stirred at 4° C. to RT for 15 h under nitrogen
2. customThe solvent was evaporated
3. customthe obtained residue was partitioned between EtOAc (150 mL) and 1N NaOH (50 mL)
4. washThe organic layer was washed with brine (20 mL)
5. dry with materialdried over MgSO4
6. filtrationfiltered
7. customevaporated

ORD record

ord-769707f543c84534b56b927174f72c4f

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08168631B2