Trifluoroacetic acid → [4-Fluoro-3-(3-morpholin-4-ylprop-1-ynyl)phenyl]-methylamine

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Reaction Steps

To a mixture of (tert-butoxy)-N-{[4-fluoro-3-(3-hydroxyprop-1-ynyl)phenyl]methyl}carboxamide (0.23 g, 0.82 mmol) (Step B) and NMO (0.14 g, 1.3 mmol) was added catalytic amount of TPAP. The resulting mixture was stirred for 1 h at RT, then filtered over a short pad of SiO2 and concentrated. To a solution of the residue and morpholine (0.1 mL, 1.2 mmol) in CH2Cl2 was added excess NaBH(OAc)3. The resulting solution was stirred for 16 h, diluted with CH2Cl2 and saturated aq. NaHCO3 solution. The organic layer was separated, dried over Na2SO4, and concentrated. The residue was purified by SiO2 chromatography to give a colorless oil, which was dissolved in 5 mL of CH2Cl2. To the organic solution was added TFA (2 mL). The resulting solution was stirred for 1 h at RT, then concentrated. The residue was diluted with CH2Cl2 and saturated aq. NaHCO3 solution. The organic layer was separated, dried over Na2SO4, and concentrated to give the title compound. MS (ES+): 249 (M+H)+; (ES−): 247. Calc'd C14H17FN2O-248.30.

Provenance & Evidence