Tetrabutylammonium Fluoride → HCID 86587203, compound

Participants

Reaction Steps

Tetrabutylammonium fluoride (TBAF) (1.24 μmol, 1.24 mL, 1 M in THF) was added to a mixture of 2-oxo-2,3-dihydrobenzoxazole-6-carbothioic acid [3-(4-benzylpiperidin-1-yl)-2-(tert-butyldimethylsilanyloxy)propyl]amide (336 mg, 623 μmol) and 4 Å molecular sieves (1 g) in THF (2 mL). After stirring at room temperature for 1.5 hours, the mixture was diluted with EtOAc, washed with saturated NaHCO3, brine and dried (MgSO4) to yield 2-oxo-2,3-dihydrobenzoxazole-6-carbothioic acid [3-(4-benzylpiperidin-1-yl)-2-hydroxypropyl]amide (280 mg, quantitative) as a solid yellow foam:

Provenance & Evidence