Tetrabutylammonium Fluoride → 2'-[(t-Butoxycarbonylamino)methyl]-1,1-biphenyl-4-methanol

Participants

Reaction Steps

To a solution of 150 mg (0.35 mmol) of 2'-[(t-butoxycarbonylamino)methyl]-4-[(t-butyldimethylsiloxy)-methyl]-1,1'-biphenyl (Step G) in 2 mL of dry tetrahydrofuran under a nitrogen atmosphere was added by syringe 0.52 mL (0.53 mmol) of 1.0M solution of tetra-n-butylammonium fluoride in tetrahydrofuran. The reaction mixture was stirred for one hour then diluted with 100 mL of ethyl acetate. The mixture was washed with water (3×20 mL), then saturated aqueous sodium chloride, dried over magnesium sulfate and filtered. The solvent was removed under vacuum to give an oil which was purified by column chromatography on silica gel eluting with hexanes/ethyl acetate (55:45) to afford 101 mg (93%) of the product as a white solid. FAB-MS: calculated for C19H23NO3 313; found 314 (M+H). 1H NMR (200 MHz, CDCl3): 1.40 (s, 9H), 2.50 (s, 2H), 4.20 (s, 2H), 4.70 (s, 2H), 7.18-7.45 (s, 8H).

Provenance & Evidence