Methyl 3-(nitromethyl)hexanoate → 4-Propylpyrrolidin-2-one

Platinum oxide (0.4 g) was added to a solution of methyl 3-(nitromethyl)hexanoate (3.64 g, 19.2 mmol) in ethanol (20 ml) was added and the mixture was stirred at room temperature for 18 hours under a hydrogen stream. The reaction mixture was filtered through celite, and then the solvent of the filtrate was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate, ethyl acetate: methanol) to yield the title compound (1.63 g) as a light yellow oil. 1H-NMR (CDCl3) δ(ppm) 0.92 (3H, t, J=7.2 Hz), 1.27-1.53 (4H, m), 1.93-2.05 (1H, m), 2.37-2.53 (2H, m), 3.01 (1H, dd, J=9.2 Hz, 6.4 Hz), 3.48 (1H, dd, J=9.2 Hz, 9.2 Hz), 5.67-5.97 (1H, m)

1. additionwas added
2. filtrationThe reaction mixture was filtered through celite
3. distillationthe solvent of the filtrate was distilled off under reduced pressure
4. customThe residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate, ethyl acetate: methanol)

ORD record

ord-62ea25c4f813430b993b0b4b04a2fb4a

Source dataset

uspto-grants-2009_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07476688B2