1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 67435329, compound

Participants

Reaction Steps

tert-Butyl (4S)-4-[2-(chloromethyl)-1H-imidazo[4,5-c]quinolin-1-yl]-5-[(methylsulfonyl)amino]pentylcarbamate (8.08 g, 16.3 mmol) was dissolved in 200 mL of CH2Cl2 and treated with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) (2.91 mL, 19.5 mmol) After 1 hour, the reaction mixture was washed successively with H2O and brine and the organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure. Chromatography (SiO2, 3% methanol/CHCl3) gave tert-butyl 3-[(11S)-9-(methylsulfonyl)-8,9,10,11-tetrahydropyrazino[1′,2′:1,2]imidazo[4,5-c]quinolin-11-yl]propylcarbamate (6.16 g) as a light yellow foam.

Provenance & Evidence