Isoamylamine → HCID 57671248, compound

HRID 731280Notes

Reaction equation

HRID 731280 reaction equation
O=[C:2]1[CH2:6][CH2:5][CH2:4][CH:3]1[C:7]([O:9][CH2:10][CH3:11])=[O:8].[CH2:12]([NH2:17])[CH2:13][CH:14]([CH3:16])[CH3:15]>C(O)C>[CH2:10]([O:9][C:7]([C:3]1[CH2:4][CH2:5][CH2:6][C:2]=1[NH:17][CH2:12][CH2:13][CH:14]([CH3:16])[CH3:15])=[O:8])[CH3:11]

Participants

4

Reactant 2

HCID 7894IsoamylamineHCID 69136Ethyl 2-oxocyclopentanecarboxylate

Product 1

HCID 57671248HCID 57671248, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of ethyl 2-oxocyclopentanecarboxylate (5.00 mL, 32.1 mmol) in ethanol (50 mL) was added isoamylamine (3.8 mL, 32.3 mmol) at 25° C. The mixture was heated at reflux for 12 h. The reaction mixture was allowed to cool to 25° C. and concentrated in vacuo. The crude material was purified by flash column chromatography (Teledyne Isco RediSep Flash Column; 0-30% ethyl acetate in hexanes) to afford the desired product, 2-(3-methylbutylamino)-cyclopent-1-enecarboxylic acid ethyl ester (6.84 g, 30.4 mmol, 95%), as a yellowish oil. 1H NMR (400 MHz, CDCl3) δ 0.92 (6H, d, J=6.1 Hz), 1.28 (3H, t, J=6.9 Hz), 1.44 (2H, q, J=7.2 Hz), 1.63-1.74 (1H, m), 1.80-1.87 (2H, m), 2.50-2.58 (4H, m), 3.19 (2H, q, J=6.7 Hz), 4.14 (2H, q, J=7.1 Hz), 7.34 (1H, bs).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 12 h
  3. concentrationconcentrated in vacuo
  4. customThe crude material was purified by flash column chromatography (Teledyne Isco RediSep Flash Column; 0-30% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-6be8f5dd58c64f89be2c515823935ff5
Source dataset
uspto-grants-2009_09
Patent number
US07582626B2

Reaction notes

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