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

Temperature

0 °C

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 (1 H, s), 7.48 (1 H, s), 7.26 (1 H, d, J=8.6 Hz), 7.17 (1 H, t, J=7.8 Hz), 6.89 (1 H, d, J=7.4 Hz), 5.12 (1 H, t, J=5.7 Hz), 4.42 (2 H, d, J=5.5 Hz), 1.47 (9 H, s)

1. temperatureto slowly warm to room temperature
2. customThe reaction was then quenched with a 50% AcOH
3. concentrationNext, the mixture was concentrated to reduced volume
4. additionpoured into a saturated sodium bicarbonate solution (75 mL)
5. extractionThe mixture was then extracted with EtOAc (2×250 mL)
6. washwashed with saturated sodium bicarbonate solution (1×75 mL), brine (1×75 mL)
7. dry with materialdried over magnesium sulfate
8. concentrationThe filtrate was concentrated
9. customthe residue was purified by medium pressure chromatography (silica gel, 0 to 5% MeOH:DCM)

ORD record

ord-9f1251217c6a44e1992d7a75de18db1d

Source dataset

uspto-grants-2011_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08003648B2