Ammonium Acetate → Methyl 2-amino-5,5-dimethylcyclohex-1-enecarboxylate

HRID 240995Notes

Reaction equation

HRID 240995 reaction equation
O[C:2]1[CH2:7][CH2:6][C:5]([CH3:9])([CH3:8])[CH2:4][C:3]=1[C:10]([O:12][CH3:13])=[O:11].C([O-])(=O)C.[NH4+:18]>C(O)C>[NH2:18][C:2]1[CH2:7][CH2:6][C:5]([CH3:9])([CH3:8])[CH2:4][C:3]=1[C:10]([O:12][CH3:13])=[O:11]

Participants

4

Reactant 2

HCID 517165Ammonium AcetateHCID 54676124Methyl 2-hydroxy-5,5-dimethylcyclohex-1-enecarboxylate

Product 1

HCID 66820389Methyl 2-amino-5,5-dimethylcyclohex-1-enecarboxylateYield 75%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of methyl 2-hydroxy-5,5-dimethylcyclohex-1-enecarboxylate (10.0 g, 54 mmol) and ammonium acetate (10 g, 130 mmol) in ethanol (50 mL) was heated to reflux for 2 hours. The reaction was concentrated to one third original volume, and then diluted with ethyl acetate (100 mL). The organic solution was washed with water (100 mL) and brine (50 mL) and then dried over anhydrous sodium sulfate. After filtration and concentration, the residue was purified by silica gel column chromatography (ethyl acetate/hexanes, 1:8) to afford methyl 2-amino-5,5-dimethylcyclohex-1-enecarboxylate (7.42 g, 75% yield) as a yellow solid. MS (EI) for C10H17NO2: 184 (MH+).

Workup

  1. temperatureto reflux for 2 hours
  2. concentrationThe reaction was concentrated to one third original volume
  3. additiondiluted with ethyl acetate (100 mL)
  4. washThe organic solution was washed with water (100 mL) and brine (50 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationAfter filtration and concentration
  7. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexanes, 1:8)

Sources & evidence

ORD record
ord-480ddb7ec6be479e9bf452fc258b24b4
Source dataset
uspto-grants-2014_02
Patent number
US08648066B2

Reaction notes

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