Acetic Acid → tert-butyl 2-(3-(5-(2-methoxyphenethoxy)-3-(trifluoromethyl)-1H-pyrazol-1-yl)benzylamino)ethyl(methyl)carbamate

Participants

Reaction Steps

To a solution of 131 (85 mg, 0.219 mmol) in THF (0.4 mL) at 0° C. under nitrogen was added BH3 in THF (1.114 mL, 1.0M solution, 1.114 mmol). The reaction was stirred at room temperature for 1 hour then it was cooled to at 0° C. and quenched carefully with methanol. The mixture was concentrated, MeOH (1.5 mL), tert-butyl methyl(2-oxoethyl)carbamate (38.0 mg, 0.219 mmol) and acetic acid (25.1 μL, 0.439 mmol) were added and the mixture was stirred at room temperature for 1 h after which sodium cyanoborohydride (34.5 mg, 0.549 mmol) was added. After 16 h, the reaction was worked-up as usual and the residue was purified by silica gel chromatography (Biotage 12M, 0-5% MeOH/DCM) to give 132 (29.3 mg, 0.053 mmol, 24.34% yield) as clear oil. LRMS(ESI): (calc.) 548.6 (found) 549.2 (MH)+.

Provenance & Evidence