Ammonium Acetate → Methyl 2-amino-5-isopropylcyclopent-1-enecarboxylate

HRID 529150Notes

Reaction equation

HRID 529150 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

HCID 517165Ammonium AcetateHCID 12840254HCID 12840254, compound

Product 1

HCID 68735644Methyl 2-amino-5-isopropylcyclopent-1-enecarboxylateYield 61%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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.

Workup

  1. customThe solvents were removed under reduced pressure
  2. washThe combined organics were washed with brine, dried Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude residue was purified by column chromatography (5

Sources & evidence

ORD record
ord-a1ab366b60fc402380f2e367c636d4a0
Source dataset
uspto-grants-2016_05
Patent number
US09346805B2

Reaction notes

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