Allyl bromide → HCID 10846824, compound

Temperature

-78 °C

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).

1. customthen quenched with acetic acid (0.5 mL)
2. additionThe reaction mixture was diluted with ethyl acetate
3. washwashed with water, brine
4. dry with materialdried over sodium sulfate
5. filtrationfiltered
6. concentrationconcentrated under reduced pressure
7. customThe residue was purified on ISCO (0-100% ethyl acetate/hexanes)

ORD record

ord-c5196937f5224b94989a8a8532cedf6c

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09169240B2