Tetrabutylammonium Fluoride → (2S,5R)-2-(hydroxymethyl)-4-methyl-6-(prop-2-en-1-yloxy)-1,6-diazabicyclo[3.2.1]oct-3-en-7-one

Participants

Reaction Conditions

Reaction Steps

To a solution of (2S,5R)-6-(allyloxy)-2-((tert-butyldimethylsilyloxy)methyl)-4-methyl-1,6-diazabicyclo[3.2.1]oct-3-en-7-one (Intermediate 13, 1.76 g, 5.20 mmol) in THF (20 mL) at 0° C. was added tetrabutylammonium fluoride (1M in THF) (6.76 mL, 6.76 mmol). Stirred at 0° C. for 1 hour. The reaction mixture was concentrated onto silica gel. Silica gel chromatography (50%-100% ethyl acetate/hexanes) afforded the desired product (1.070 g, 92%) as a colorless oil.

Provenance & Evidence