Ammonium Acetate → Methyl 2-amino-5-isopropylcyclopent-1-enecarboxylate
Reaction equation
[CH:1]([CH:4]1[CH2:8][CH2:7][C:6](=O)[CH:5]1[C:10]([O:12][CH3:13])=[O:11])([CH3:3])[CH3:2].C([O-])(=O)C.[NH4+:18]>CO>[NH2:18][C:6]1[CH2:7][CH2:8][CH:4]([CH:1]([CH3:3])[CH3:2])[C:5]=1[C:10]([O:12][CH3:13])=[O:11]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
A solution of methyl 2-isopropyl-5-oxocyclopentanecarboxylate (5.4 g, 29.31 mmol) in MeOH (145 mL) was treated with ammonium acetate (22.59 g, 293.1 mmol), and the mixture was heated to 50° C. for 2 hours and stirred at room temperature overnight. The solvents were removed under reduced pressure, and the crude residue was taken up in DCM and H2O. The combined organics were washed with brine, dried Na2SO4, filtered, and concentrated. The crude residue was purified by column chromatography (5 then 15% EtOAc/Hexane) to yield pure methyl 2-amino-5-isopropylcyclopent-1-enecarboxylate (3.27 g, 61%). LCMS (APCI+) m/z 184.0 [M+H]+; Rt=3.51 min.