Acetic Acid → HCID 54299104, compound

Participants

Reaction Steps

9.9 g (42.42 mmol) of the aziridine ethyl (2R,3S)-3-mesityl-aziridine-2-carboxylate were dissolved in a high pressure reactor in 300 mL of methanol, and 990 mg of Pd/C and 10 mL of acetic acid (84.84 mmol) were added next. The system was purged with vacuum/nitrogen cycles and then the reactor was pressurized with 40 bar of hydrogen. The reaction mixture was maintained under stirring at room temperature for 48 hours. After this time, the catalyst was removed by means of celite filtration and the resulting solution was concentrated under reduced pressure. Compound (IIa) was obtained quantitatively in the form of a yellow solid. Mp 81-83° C. [α]D=−26.7 (c 1.00, CHCl3). IR (film): ν max 2918, 1742, 1612, 1483, 1225. 1H NMR (400 MHz, CDCl3) δ: 6.84 (s, 2H), 5.61 (b, 1H), 4.14 (m, 2H), 3.77 (dd, 1H, J=6.4 and 7.6 Hz), 3.08 (m, 2H), 2.94 (m, 2H), 2.31 (s, 6H), 2.25 (s, 3H), 1.18 (t, 3H, J=7 Hz) ppm. 13C NMR (100 MHz, CDCl3) δ178.9 (CO), 137.1 (C), 136.3 (C), 131.1 (C), 129.5 (CH), 129.5 (CH), 129.2 (C), 61.4 (CH2), 54.1 (CH), 34.6 (CH2), 24.9 (CH3), 21.0 (CH3), 19.8 (CH3), 14.2 (CH3) ppm. EM (ESI+) m/z: 236.2 [(M+H)+, 100%]. HRMS (ESI+): Calculated for C14H22NO2: 236.1645, 236.1637 found.

Provenance & Evidence