Tetrabutylammonium Fluoride → HCID 59437163, compound

Participants

Reaction Steps

TBAF (400 mg, 1.6 mmol) was added to a solution of (S)-4-((tert-butyldiphenylsilyloxy)methyl)-1-(1-adamantylmethyl)imidazolidin-2-one (261 mg, 0.52 mmol) in anhydrous THF (5 mL) at 0° C. The reaction was stirred at rt overnight. The reaction solution was concentrated to give the residue, which was purified by preparative TLC (PE/EtOAc 1/1) to provide (S)-1-(1-adamantylmethyl)-4-(hydroxymethyl)imidazolidin-2-one (45 mg, 10%). 1H NMR: (CDCl3, 400 MHz): δ=1.54 (s, 6H), 1.62-1.73 (m, 6H), 1.98 (s, 3H), 2.77 (m, 2H), 3.35 (m, 1H), 3.55-3.75 (m, 3H), 3.82 (m, 1H); MS m/z=265

Provenance & Evidence