Acetic Acid → HCID 57832619, compound

HRID 731232Notes

Reaction equation

HRID 731232 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH2:7])=[CH:4][CH:3]=1.[CH2:10]([O:12][C:13]([CH:15]1[CH2:19][CH2:18][CH2:17][C:16]1=O)=[O:14])[CH3:11].C(O)(=O)C>C1(C)C=CC=CC=1>[CH2:10]([O:12][C:13]([C:15]1[CH2:19][CH2:18][CH2:17][C:16]=1[NH:7][CH2:6][C:5]1[CH:8]=[CH:9][C:2]([F:1])=[CH:3][CH:4]=1)=[O:14])[CH3:11]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 673264-FluorobenzylamineHCID 69136Ethyl 2-oxocyclopentanecarboxylate

Product 1

HCID 57832619HCID 57832619, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
70 °C

Procedure

4-Fluorobenzylamine (12.1 g, 97.5 mmol) was added to a solution of 2-oxo-cyclopentanecarboxylic acid ethyl ester (15.25 g, 97.6 mmol) in toluene (225 mL) at 23° C. Glacial acetic acid (6.15 mL, 107 mmol) was then added, producing a large amount of white solid. The reaction mixture was heated to 70° C. in an oil bath, whereupon most of the solids dissolved. After stirring for 2 h at 70° C., a Dean-Stark apparatus and reflux condenser were fitted to the reaction flask and approximately 40 mL of liquid (predominantly toluene) was removed by distillation over 45 min (oil bath temperature=145° C.). The mixture was allowed to cool to 23° C. and was used in the next step. A small aliquot of the crude reaction mixture was concentrated under reduced pressure to afford the desired product, 2-(4-fluoro-benzylamino)-cyclopent-1-enecarboxylic acid ethyl ester as an orange oil: 1H NMR (CDCl3) δ: 1.28 (3H, t, J=7.5), 1.79-1.86 (2H, m), 2.51-2.56 (4H, m), 4.15 (2H, q, J=6.9), 4.34-4.36 (2H, m), 6.98-7.03 (2H, m), 7.19-7.23 (2H, m), 7.73 (1H, bs).

Workup

  1. customproducing a large amount of white solid
  2. dissolutionwhereupon most of the solids dissolved
  3. temperaturea Dean-Stark apparatus and reflux condenser
  4. customwas removed by distillation over 45 min (oil bath temperature=145° C.)
  5. temperatureto cool to 23° C.
  6. customA small aliquot of the crude reaction mixture
  7. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-b043e116ac824be4a6b788b83554b6bf
Source dataset
uspto-grants-2009_09
Patent number
US07582626B2

Reaction notes

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