Pyrrolidine → HCID 70559553, compound
Reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:12][C:13]([OH:15])=O)[CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10].[NH:16]1[CH2:20][CH2:19][CH2:18][CH2:17]1.C(N(C(C)C)CC)(C)C>S(Cl)(Cl)=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:12][C:13]([N:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)=[O:15])[CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of the product of EXAMPLE 30B (1 g, 4.74 mmol) in thionyl dichloride (20 mL) was stirred at reflux for 3 hours. The solution was concentrated and the residue was diluted with dry dichloromethane (20 mL) and dropped into a solution of pyrrolidine (0.63 mL, 7.1 mmol) and diisopropyl ethylamine (1.7 mL, 9.5 mmol). The mixture was stirred at room temperature overnight and the mixture was washed with 1N aqueous hydrochloric acid (20 mL) and brine. The organic phase was dried over anhydrous sodium sulfate, filtered and concentrated and the residue was purified by flash chromatography on silica gel eluting with 1/100 methanol/dichloromethane to give the title compound.