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

Participants

Reaction Conditions

Reaction Steps

Into a 100-mL round-bottom flask, was placed tetrahydrofuran (30 mL), (2S,5R)-2-[[(tert-butyldimethylsilyl)oxy]methyl]-3-methyl-6-(prop-2-en-1-yloxy)-1,6-diazabicyclo[3.2.1]oct-3-en-7-one (Intermediate 148, 3.2 g, 9.45 mmol, 1.00 equiv) and it was cooled to 0° C., then TBAF (14.2 mL 1N in THF, 1.50 equiv) was added dropwise. The resulting solution was stirred for 1 h at 0° C. in a water/ice bath. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:5-1:2). This resulted in 1.6 g (75%) of the title compound as a light yellow solid.

Provenance & Evidence