1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 86675581, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 1,8-diazabicyclo[5.4.0]undec-7-ene (10.6 g, 10.5 ml, 69.6 mmol, Eq: 1.04) in THF (59.0 ml) at 5° C. was added dropwise a solution of allyl 2-(3-nitrophenyl)acetate (intermediate B3a) (14.8 g, 66.9 mmol, Eq: 1.00) and 4-acetamidobenzenesulfonyl azide (16.6 g, 68.9 mmol, Eq: 1.03) in THF (118 ml) within 40 min and the mixture was stirred at 23° C. for 18 h protected from light. Quenched with sat. NH4Cl-sol., diluted with ethyl acetate, separated phases, the organic layer was washed with brine and dried over Na2SO4. Removal of the solvent in vacuum left an orange semisolid, diluted with diethyl ether, filtered the solid off, washed with diethyl ether, the filtrate was concentrated in vacuum to give an orange semisolid. The crude material was purified by flash chromatography (silica gel, 300 g, 25% to 30% EtOAc in heptane) to give the title compound as a yellow solid (15.62 g, 94%).

Provenance & Evidence