1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 9948631, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of compound 2A (410 mg, 1.29 mmol) and DBU (0.2 mL, 1.33 mmol) in toluene (10 mL) was heated at 80° C. for 2 hours. HPLC check of the reaction showed little product formed. Additional DBU (0.1 mL) was added and the reaction heated at 90° C. overnight. After cooling to RT, the reaction mixture was filtered. The filtrate was diluted with EtOAc, washed with 1 N aqueous HCl, water, brine, dried over MgSO4 and concentrated under reduced pressure to give a crude product, which was chromatographed (silica gel) eluting with CH2Cl2, 0.2% to 0.4% MeOH in CH2Cl2 to give the title compound (racemate) (80 mg) as a brown solid. mp. 215-217° C. HPLC: 97.5% at 2.51 min (retention time) (YMC S5 ODS column 4.6×50 mm; 10-90% aqueous methanol over 4 minutes containing 0.2% phosphoric acid, 4 mL/min, monitoring at 220 nM), MS (ES): m/z 312 [M+1]+.

Provenance & Evidence