1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 86695586, compound
Reaction equation
CS(O[CH:6]1[CH2:12][C@@H:11]2[N:13]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C@@H:8]([CH2:9][CH2:10]2)[CH:7]1[C:21]([O:23][CH3:24])=[O:22])(=O)=O.C1CCN2C(=NCCC2)CC1>CN(C=O)C>[C@H:8]12[N:13]([C:14]([O:16][C:17]([CH3:18])([CH3:19])[CH3:20])=[O:15])[C@H:11]([CH2:10][CH2:9]1)[CH2:12][CH:6]=[C:7]2[C:21]([O:23][CH3:24])=[O:22]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
(1S,5R)-8-tert-butyl 2-methyl 3-(methylsulfonyloxy)-8-azabicyclo[3.2.1]octane-2,8-dicarboxylate (14.22 g, 39.15 mmol) and DBU (58.55 mL, 391.15 mmol) in DMF (73.87 mL) were heated at 100° C. for 10 hours. The reaction was quenched with saturated sodium bicarbonate solution and extracted with ethyl acetate. The organic fractions were combined, dried with sodium sulfate and concentrated to give crude product. The crude was purified using flash chromatography (0-100% Ethyl Acetate in Hexane) to give 5.45 g of (1S,5R)-8-tert-butyl 2-methyl 8-azabicyclo[3.2.1]oct-2-ene-2,8-dicarboxylate.