Allyl bromide → HCID 10846824, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of tert-butyl 2-oxopyrrolidine-1-carboxylate (1.26 g, 6.80 mmol) at −78° C., was added lithiumdiisopropyl amine (4.76 mL, 9.52 mmol) (2 M in heptane/THF/benzene) dropwise over 15 minutes. After 15 min, allyl bromide (1.18 mL, 13.6 mmol) was added and the reaction stirred at −78° C. for 1 h then quenched with acetic acid (0.5 mL). The reaction mixture was diluted with ethyl acetate, washed with water, brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified on ISCO (0-100% ethyl acetate/hexanes) to afford Compound 1a (550 mg, 36%) as a clear oil. LCMS=1.95 min using analytical Method (B), 473.4 (2M+Na). 1H NMR (400 MHz, CDCl3-d) δ 5.89-5.69 (m, 1H), 5.18-5.00 (m, 2H), 3.76 (ddd, J=11.2, 8.5, 2.9 Hz, 1H), 3.58 (ddd, J=10.8, 9.0, 7.5 Hz, 1H), 2.70-2.50 (m, 2H), 2.29-2.07 (m, 2H), 1.79-1.64 (m, 1H), 1.53 (s, 9H).

Provenance & Evidence