Ammonia → 3-(Aminomethyl)-1,3-dihydro-2,1-benzoxaborol-1-ol hydrochloride

To a solution of 3-(nitromethyl)benzo[c][1,2]oxaborol-1(3H)-ol (965 mg, 5 mmol) in ethanol (30 mL) were added ammonia (2M solution in ethanol, 18 mL, 36 mmol) and Raney 2800 Nickel (⅓ teaspoon of a slurry in water). The reaction mixture was subjected to hydrogenation at 45 atmospheres for 2 h at rt. The resulting mixture was filtered through Celite and the filtrate was concentrated in vacuo yielding the crude amine. The amine was dissolved in dioxanes (10 mL) and HCl (4M in dioxanes, 5 mL, 20 mmol) was added. After 1 h, the suspension was concentrated and the resulting solid was washed with hexanes followed by ether yielding 3-(aminomethyl)benzo[c][1,2]oxaborol-1(3H)-ol hydrochloride (917 mg, 4.6 mmol, 92% yield) as a white solid.

1. filtrationThe resulting mixture was filtered through Celite
2. concentrationthe filtrate was concentrated in vacuo
3. customyielding the crude amine
4. waitAfter 1 h
5. concentrationthe suspension was concentrated
6. washthe resulting solid was washed with hexanes

ORD record

ord-6397a3afe74e4b3d8451375c8f6714e5

Source dataset

uspto-grants-2010_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07816344B2