N-bromobutanimide → HCID 11694443, compound

Participants

Reaction Conditions

Reaction Steps

The product of step f) was dissolved in 2 mL of 1:1 CHCl3/HOAc and treated with NBS (62 mg, 0.35 mmol). After stirring for 10 minutes, the reaction was concentrated to dryness and filtered through a pad of silica gel, eluting with EtOAc. The eluent was concentrated and the residue was treated with 2 mL each EtOH and 40% aqueous KOH. After heating for 14 hours at 100° C., the reaction was diluted with water and extracted 2× into DCM. The title compound was purified by preparative HPLC-MS. The two enantiomers were separated using a Chiralpak® AD-RH® 20×250 mm column from Chiral Technologies (10 mL/min MeOH mobile phase) to give enantiomer 1 (rt=11.6 minutes) and enantiomer 2 (rt=13.6 minutes) of the title compound. 1H NMR (CD3OD) δ 6.92 (s, 1H), 3.48-3.34 (m, 3H), 3.17-2.99 (m, 4H), 1.44 (d, J=7.2 Hz, 3H); MS: ESI (positive): 246, 248 (M+H).

Provenance & Evidence