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

HRID 82419Notes

Reaction equation

HRID 82419 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-f4efb1fb80494d20ba425f9689390ddf
Source dataset
uspto-grants-2014_09
Patent number
US08846681B2

Reaction notes

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