Water → tert-Butyl 4-((1-(6-chloro-1-methyl-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-4-yl)ethoxy)methyl)-4-(4-fluorophenyl)piperidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

tert-Butyl 4-((1-(6-chloro-1-methyl-2-oxo-3-((2-(trimethylsilyl)ethoxy)methyl)-2,3-dihydro-1H-benzo[d]imidazol-4-yl)ethoxy)methyl)-4-(4-fluorophenyl)piperidine-1-carboxylate (53 mg, 0.082 mmol) was dissolved in tetrabutylammonium fluoride (1M in tetrahydrofuran, 1 mL, 1 mmol) and immersed in an oil bath which was pre-heated to 60° C. After 1.5 h, the temperature was increased to 65° C. and stirred at that temperature for 5 h. The reaction was sealed and heated at 70° C. overnight. The crude reaction mixture was diluted with diethyl ether and poured into water. The ethereal was washed with water (2×), then brine, dried over magnesium sulfate and concentrated. Column chromatography (25%→75% ethyl acetate/n-hexane) gave 26 mg (61%) as a colorless film. 1H-NMR (CDCl3, 500 MHz) δ 7.66 (bs, 1H), 7.25 (dd, J=8.6, 5.5 Hz, 2H), 7.05 (dd, J=8.9, 8.6 Hz, 2H), 6.80 (d, J=1.5 Hz, 1H), 6.66 (d, J=1.8 Hz, 1H), 4.29 (q, J=6.7 Hz, 1H), 3.73 (m, 2H), 3.32 (d, J=9.2 Hz, 1H), 3.31 (s, 3H), 3.27 (d, J=9.2 Hz, 1H), 2.87-3.12 (m, 2H), 2.20 (m, 1H), 2.06 (m, 1H), 1.81 (m, 1H), 1.74 (bs, 1H), 1.43 (s, 9H), 1.32 (d, J=6.4 Hz, 3H). Mass spec.: 540.10 (MNa)+.

Provenance & Evidence