Tetrabutylammonium Fluoride → HCID 59730221, compound

Participants

Reaction Steps

Treat (±)-(trans)-6-(4-{2-[3-(tert-butyldimethyl-silyloxy)cyclohexylamino]ethyl}phenoxy)nicotinamide (Example 451, Part C, 63.3 mg, 0.13 mmol) in THF (1.0 mL) with 1:0 M tetrabutylammonium fluoride (TBAF) in THF (0.5 eq) for 1 hour. Add another 0.5 eq of 1.0 M TBAF and stir for 4 hours. Add 1.0 eq of 1.0 M TBAF and stir for 9 days. Add another 1.0 eq of 1.0 M TBAF and stir for 4 days. Concentrate, dissolve the mixture in CH2Cl2 (20 mL), and wash with H2O (2×20 mL), saturated aqueous NaHCO3 and brine (20 mL each). Back-extract the aqueous layers with CH2Cl2 (20 mL). Concentrate the two H2O washings and purify by flash chromatography, eluting with 15% (2.0 M NH3 in MeOH) in CH2Cl2 to afford the title compound (42.1 mg, 88%): MS ES+ 356.4 (M+H)+, HRMS calcd for C21H28N3O2 356.1974 (M+H)+, found 356.1979, time 0.41 min; HPLC [YMC-Pack Pro C-18 (150×4.6 mm, S-5 microm), 0.1% TFA/acetonitrile in 0.1% TFA/water at 1.0 mL/min, 5-99% over 19 min], tR=7.11 min, 100% purity.

Provenance & Evidence