Water → Ethyl 4-amino-2-methylcyclohexane-1-carboxylate

HRID 2390999Notes

Reaction equation

HRID 2390999 reaction equation
[CH3:1][C:2]1[CH:3]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:4][CH2:5][C:6](=O)[CH:7]=1.O.C([O-])=O.[NH4+:18]>CO.[Pd]>[NH2:18][CH:6]1[CH2:5][CH2:4][CH:3]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:2]([CH3:1])[CH2:7]1

Participants

6

Reactant 3

HCID 962WaterHCID 790204-Carbethoxy-3-methyl-2-cyclohexen-1-oneHCID 2723923Ammonium formate

Product 1

HCID 57465891Ethyl 4-amino-2-methylcyclohexane-1-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Ethyl 2-methyl-4-oxocyclohex-2-enecarboxylate (2.0 g, 10.98 mmol) is dissolved in MeOH (40 ml) and water (4.0 ml) to give a yellow solution. Ammonium formate (8.31 g, 132 mmol) is added and stirred at RT until the suspension dissolves to form a solution. Palladium on carbon (0.117 g, 1.098 mmol) is added and the reaction mixture is stirred at 70° C. for 1 hour. The mixture is filtered through Celite® (filter material) and washed with MeOH. The filtrate is concentrated in vacuo and the residue is partitioned between EtOAc and water. The aqueous portion is diluted with sat. sodium bicarbonate and washed with EtOAc. The pH is adjusted to pH 14 using 1M NaOH and the aqueous is extracted with EtOAc. The combined organic extracts are dried MgSO4, filtered and concentrated in vacuo to afford the title compound; [MH]+ 186.24.

Workup

  1. dissolutiondissolves
  2. customto form a solution
  3. stirringthe reaction mixture is stirred at 70° C. for 1 hour
  4. filtrationThe mixture is filtered through Celite® (filter material)
  5. washwashed with MeOH
  6. concentrationThe filtrate is concentrated in vacuo
  7. customthe residue is partitioned between EtOAc and water
  8. additionThe aqueous portion is diluted with sat. sodium bicarbonate
  9. washwashed with EtOAc
  10. extractionthe aqueous is extracted with EtOAc
  11. filtrationfiltered
  12. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-dc571beb9d4a49ef8662ad35dabf73e3
Source dataset
uspto-grants-2012_09
Patent number
US08273900B2

Reaction notes

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