Hydrochloric Acid → 1-Amino-3,3-dimethylbutan-2-one hydrochloride

To a 2 L three-necked round-bottom flask fitted with a mechanical stirrer were added azidopinacolone (28.6 g, 203 mmol, 1.0 equiv), methanol (1145 mL), concentrated HCl (18 mL), and 10% Pd/C (3.5 g, 50% water wet). The reaction mixture was stirred under hydrogen at 20 psi for 2 h, the mixture was filtered through a pad of Celite, and the residue rinsed with methanol (2×50 mL). The filtrate was concentrated under reduced pressure at a temperature below 40° C. The resulting wet solid was azeotroped with 2-propanol (2×100 mL), anhydrous ether (100 mL) was added, and the slurry which formed was stirred for 5 min. The solid product was collected by filtration, and the cake was washed with diethyl ether (2×30 mL) and then dried in vacuo to give aminopinacolone hydrochloride A-2.

1. customTo a 2 L three-necked round-bottom flask fitted with a mechanical stirrer
2. filtrationthe mixture was filtered through a pad of Celite
3. washthe residue rinsed with methanol (2×50 mL)
4. concentrationThe filtrate was concentrated under reduced pressure at a temperature below 40° C
5. customThe resulting wet solid was azeotroped with 2-propanol (2×100 mL), anhydrous ether (100 mL)
6. additionwas added
7. customthe slurry which formed
8. stirringwas stirred for 5 min
9. filtrationThe solid product was collected by filtration
10. washthe cake was washed with diethyl ether (2×30 mL)
11. customdried in vacuo

ORD record

ord-3f01f98f90394da0a7f09f81666b9dd5

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08962855B2