Tetrabutylammonium Fluoride → 4-[((2S)-3-{[4-({[5-(tert-butyl)-1,2,4-oxadiazol-3-yl]methyl}sulfonyl)phenethyl]amino}-2-hydroxypropyl)oxy]phenol

Participants

Reaction Steps

To a solution of the amino alcohol of Example 14(0.650 g, 0.90 mmol) in THF (12 mL) was added a 1 M solution of TBAF (0.225 mL, 0.225 mmol). The reaction mixture was stirred for 6 h. TLC showed the absence of starting material, therefore 5 drops of a saturated aqueous ammonium chloride solution was added. The reaction mixture was evaporated in vacuo to dryness and the residue was flash chromatographed (silica gel; dichloromethane/chloroform/methanol: 15/5/3) to afford 0.280 g of the title compound as a white foam.

Provenance & Evidence