Borane → tert-Butyl (3-(hydroxymethyl)phenyl)carbamate

Participants

Reaction Conditions

Reaction Steps

3-(tert-Butoxy-carbonylamino)benzoic acid (3.00 g, 12.6 mmol) was dissolved in THF (30 mL) and cooled to 0° C. A 1 M borane:THF solution (12.7 mL, 12.7 mmol) was slowly added to the reaction. The solution was then allowed to slowly warm to room temperature and stirred for six hours. The reaction was then quenched with a 50% AcOH:water mixture (2 mL). Next, the mixture was concentrated to reduced volume and poured into a saturated sodium bicarbonate solution (75 mL). The mixture was then extracted with EtOAc (2×250 mL). The organic layers were combined and washed with saturated sodium bicarbonate solution (1×75 mL), brine (1×75 mL), and then dried over magnesium sulfate. The filtrate was concentrated, and the residue was purified by medium pressure chromatography (silica gel, 0 to 5% MeOH:DCM) to give 27.1 (2.41 g). MS ESI (pos.) m/e 241.1 (M+18). 1H NMR (400 MHz, DMSO-d6) δ ppm 9.28 (1H, s), 7.48 (1H, s), 7.26 (1H, d, J=8.6 Hz), 7.17 (1H, t, J=7.8 Hz), 6.89 (1H, d, J=7.4 Hz), 5.12 (1H, t, J=5.7 Hz), 4.42 (2H, d, J=5.5 Hz), 1.47 (9H, s)

Provenance & Evidence