N-bromobutanimide → HCID 10202424, compound

Participants

Reaction Steps

The product from Example 97B (0.77 g, 1.7 mmol) in chloroform (30 mL) under nitrogen was treated with N-bromosuccinimide (0.36 g, 2.0 mmol), stirred at ambient temperature for 30 minutes, refluxed for 16 hours and concentrated to dryness. The resulting two isomers were separated by chromatography on silica gel eluting with (ethyl acetate:formic acid:water:hexane, 38:1:1:40 to 38:1:1:30 to 38:1:1:20). The faster moving isomer was rechromatographed on silica gel eluting with 2% methanol in ammonia saturated dichloromethane and then rechromatographed again on silica gel eluting with (hexanes:acetone, 3:1). The faster moving isomer was then crystallized from acetone/hexanes and the resulting crystals were collected by filtration, washed with acetone/hexanes and dried under reduced pressure to provide the title compound (0.058 g).

Provenance & Evidence