Tris(hydroxymethyl)aminomethane → Tert-butyl 2-methylbutanoate

To a stirred solution of 2-methylbutanoic acid (1.029 Ml, 8.29 mmol) in DCM (10 Ml) was added potassium tert-butoxide (20 wt % in THF) (4.66 Ml, 8.29 mmol) dropwise at 0° C. The resulting suspension was allowed to warm to room temperature, and stirred for 1.5 hr. The reaction mixture was diluted with DCM (10 Ml), MP-®Trisamine Resin (3.86 g, 3.22 mMol/g; Argonaut Technologies, Inc.) was added, and the resulting suspension was stirred at room temperature for 1.5 hours. The resin was removed by vacuum filtration, and the resulting filtrate was washed with 1 N NaOH (1×20 Ml). The organic layer was dried over magnesium sulfate, filtered, and concentrated to afford tert-butyl 2-methylbutanoate. 1H NMR (500 MHz, CDCl3) δ 2.24 (sextet, 1H), 1.61 (m, 1H), 1.44-1.39 (overlapping s, m, 10H), 1.09 (d, 3H), 0.90 (t, 3H).

1. additionwas added
2. stirringthe resulting suspension was stirred at room temperature for 1.5 hours
3. customThe resin was removed by vacuum filtration
4. washthe resulting filtrate was washed with 1 N NaOH (1×20 Ml)
5. dry with materialThe organic layer was dried over magnesium sulfate
6. filtrationfiltered
7. concentrationconcentrated

ORD record

ord-dca8fe0f0dc64c51a32c3697e7d08d51

Source dataset

uspto-grants-2012_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08329722B2