Boron trifluoride etherate → HCID 123843496, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl(1-(4-(2-oxo-7-phenyl-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-6-yl)phenyl)cyclobutyl)carbamate (143 mg, 0.42 mmol) in dry THF (4 mL) was added boron trifluoride diethyl etherate (91 μL, 0.73 mmol) and sodium borohydride (27 mg, 0.73 mmol) at 0° C. under nitrogen. The resulting mixture was stirred for 4 h at 0° C. AcOEt (5 mL) and a saturated solution of NaHCO3 (10 mL) were added. The aqueous phase was extracted with dichloromethane (3×) using a phase separator (Isolute® SPE). The combined organic phases were concentrated to dryness under reduced pressure. The resulting residue was purified by Biotage silica gel chromatography (gradient 0 to 2% MeOH in DCM) to give the title compound as a white solid (66 mg, 48%). 1H NMR (500 MHz, CDCl3): 7.21-7.26 (7H, m), 7.14-7.12 (2H,m), 6.97 (1H, s), 4.48 (2H, t), 3.48 (2H, br s),2.55-2.25 (4H, m), 2.06-1.98 (1H, m), 1.82-1.73 (1H, m), 1.44-1.15 (9H, br).

Provenance & Evidence