Ammonium Acetate → Ethyl 2-amino-5-vinylcyclopent-1-enecarboxylate

HRID 1675899Notes

Reaction equation

HRID 1675899 reaction equation
O=[C:2]1[CH2:6][CH2:5][CH:4]([CH:7]=[CH2:8])[CH:3]1[C:9]([O:11][CH2:12][CH3:13])=[O:10].C([O-])(=O)C.[NH4+:18]>CO>[NH2:18][C:2]1[CH2:6][CH2:5][CH:4]([CH:7]=[CH2:8])[C:3]=1[C:9]([O:11][CH2:12][CH3:13])=[O:10]

Participants

4

Reactant 2

HCID 517165Ammonium AcetateHCID 14194531Ethyl 2-ethenyl-5-oxocyclopentane-1-carboxylate

Product 1

HCID 59682828Ethyl 2-amino-5-vinylcyclopent-1-enecarboxylateYield 41%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

Ethyl 2-oxo-5-vinylcyclopentanecarboxylate (0.48 g, 2.79 mmol) was mixed with ammonium acetate (2.15 g, 27.9 mmol) in MeOH (10 mL). The mixture was heated to 50° C. for 2 hours. The contents were concentrated. The residue was partitioned between DCM and water. The DCM layer was separated, and the aqueous layer was extracted with DCM. The combined DCM solutions were dried (Na2SO4). The crude was purified with flash chromatography to give ethyl 2-amino-5-vinylcyclopent-1-enecarboxylate (0.19 g, 41% for 2 steps). 1H NMR (CDCl3, 400 MHz) δ (ppm): 5.59-5.58 (m, 1H), 5.05-4.88 (m, 2H), 3.68 (s, 3H), 3.52-3.46 (m, 1H), 2.66-2.56 m, 1H), 2.38-2.30 (m, 1H), 2.13-2.03 (m, 1H), 1.70-1.62 (m, 1H), 1.61 (br s, 2H). MS: 168.0 (M+1).

Workup

  1. concentrationThe contents were concentrated
  2. customThe residue was partitioned between DCM and water
  3. customThe DCM layer was separated
  4. extractionthe aqueous layer was extracted with DCM
  5. dry with materialThe combined DCM solutions were dried (Na2SO4)
  6. customThe crude was purified with flash chromatography

Sources & evidence

ORD record
ord-cbb9bcd6da664b81b104fd88e4fae287
Source dataset
uspto-grants-2011_08
Patent number
US08003651B2

Reaction notes

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