3,3-Dimethylbutylamine → 2-(3,3-Dimethylbutylamino)-cyclopent-1-enecarboxylic acid ethyl ester

HRID 731284Notes

Reaction equation

HRID 731284 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].[CH3:12][C:13]([CH3:18])([CH3:17])[CH2:14][CH2:15][NH2:16]>C(O)C>[CH2:10]([O:9][C:7]([C:3]1[CH2:4][CH2:5][CH2:6][C:2]=1[NH:16][CH2:15][CH2:14][C:13]([CH3:18])([CH3:17])[CH3:12])=[O:8])[CH3:11]

Participants

4

Reactant 2

HCID 197093,3-DimethylbutylamineHCID 69136Ethyl 2-oxocyclopentanecarboxylate

Product 1

HCID 576712592-(3,3-Dimethylbutylamino)-cyclopent-1-enecarboxylic acid ethyl esterYield 89%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of ethyl 2-oxocyclopentanecarboxylate (4.10 mL, 26.3 mmol) in ethanol (50 mL) was added 3,3-dimethylbutylamine (2.80 g, 26.8 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; 0-20% ethyl acetate in hexanes) to afford the desired product, 2-(3,3-dimethylbutylamino)-cyclopent-1-enecarboxylic acid ethyl ester (5.59 g, 23.4 mmol, 89%), as a yellowish oil. 1H NMR (400 MHz, CDCl3) δ 0.94 (9H, s), 1.28 (3H, t, J=7.0 Hz), 1.46-1.50 (2H, m), 1.80-1.88 (2H, m), 2.51-2.58 (4H, m), 3.16-3.21 (2H, m), 4.14 (2H, q, J=7.0 Hz).

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; 0-20% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-7236c49426e14ce2b749850810b01a1f
Source dataset
uspto-grants-2009_09
Patent number
US07582626B2

Reaction notes

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