Ammonia → Ethyl 4-aminocyclohexanecarboxylate

HRID 1619320Notes

Reaction equation

HRID 1619320 reaction equation
O=[C:2]1[CH2:7][CH2:6][CH:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][CH2:3]1.[NH3:13]>CO.[Pd]>[NH2:13][CH:2]1[CH2:7][CH2:6][CH:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][CH2:3]1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 317638Ethyl 4-oxocyclohexanecarboxylate

Product 1

HCID 409963Ethyl 4-aminocyclohexanecarboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Ethyl 4-oxocyclohexanecarboxylate (3.0 g, 17.65 mmol) was dissolved in 150 mL methanol saturated with ammonia at 0° C., and to the solution was added wet 10% Pd/C catalyst (4.0 g). The mixture was stirred at room temperature under hydrogen (1 atm) for about 36 h. Then the catalyst was then removed by filtration and the filtrate was concentrated to give the crude product, which was purified by chromatography on silica gel to give 2.0 g of the desired product. MS (ESI): 172 (MH+).

Workup

  1. customThen the catalyst was then removed by filtration
  2. concentrationthe filtrate was concentrated
  3. customto give the crude product, which
  4. customwas purified by chromatography on silica gel

Sources & evidence

ORD record
ord-1c09787b1b344388bfd206d093fe9a73
Source dataset
uspto-grants-2014_07
Patent number
US08772301B2

Reaction notes

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