Tetrabutylammonium Fluoride → HCID 54338219, compound

Participants

Reaction Steps

Treat a solution of the crude oxime from Step 3 (≤12.3 mmol) in THF (400 mL) with TBAF (15.4 mL, 15.4 mmol, 1M in THF) at 0° C. Stir the solution for 2 hours. Quench the reaction with water and extract the aqueous phase with EtOAc (3×100 mL). Dry the combined organic layers over MgSO4, filter and concentrate under reduced pressure to give the crude product as a yellow oil. Purify by silica gel chromatography (column: 7.5 cm×20 cm; pack column in CH2Cl2 and elute using a gradient of 100% CH2Cl2 to 5% CH3 OH(NH3)/CH2Cl2) to obtain 16 g (29.9 mmol, 75% from Example CAA2) of the title compound as a white solid. HRMS (FAB, M+H+): m/e cal'd for [C23H29N2O3Cl2 ]+ : 451.1555, found 451.1553 .

Provenance & Evidence