Isoamylamine → HCID 57671214, compound

HRID 731291Notes

Reaction equation

HRID 731291 reaction equation
O=[C:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[C:8]([O:10][CH2:11][CH3:12])=[O:9].[CH2:13]([NH2:18])[CH2:14][CH:15]([CH3:17])[CH3:16]>C(O)C>[CH2:11]([O:10][C:8]([CH:3]1[CH2:4][CH2:5][CH2:6][CH2:7][CH:2]1[NH:18][CH2:13][CH2:14][CH:15]([CH3:17])[CH3:16])=[O:9])[CH3:12]

Participants

4

Reactant 2

HCID 7894IsoamylamineHCID 95543Ethyl 2-oxocyclohexanecarboxylate

Product 1

HCID 57671214HCID 57671214, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of ethyl 2-oxocyclohexanecarboxylate (3.0 mL, 17.8 mmol) in ethanol (30 mL) was added isoamylamine (2.1 mL, 17.9 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)-cyclohexanecarboxylic acid ethyl ester (3.23 g, 13.5 mmol, 76%), as a yellowish oil. LC-MS (ESI) calcd for C14H25NO2 239.19, found 240.3 [M+H+].

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-69832d48618846668494d31ffc8b51da
Source dataset
uspto-grants-2009_09
Patent number
US07582626B2

Reaction notes

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