ethyl (1R,3S)-3-benzyloxycarbonylaminocyclohexanecarboxylate → (1R,3S)-ethyl 3-aminocyclohexanecarboxylate

HRID 75030Notes

Reaction equation

HRID 75030 reaction equation
C(OC([NH:11][C@H:12]1[CH2:17][CH2:16][CH2:15][C@@H:14]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:13]1)=O)C1C=CC=CC=1>C(O)C.[Pd]>[NH2:11][C@H:12]1[CH2:17][CH2:16][CH2:15][C@@H:14]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:13]1

Participants

4

Reactant 1

HCID 68101877ethyl (1R,3S)-3-benzyloxycarbonylaminocyclohexanecarboxylate2×

Product 1

HCID 12636188(1R,3S)-ethyl 3-aminocyclohexanecarboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of (1R,3S)-ethyl 3-(benzyloxycarbonylamino)cyclohexane-carboxylate, 18b, (14.0 g, 45.9 mmol) in ethanol (3 mL) was added Pd/C (wet, Degussa (2.4 g, 2.3 mmol). The mixture was evacuated and then stirred under atmosphere of nitrogen at room temperature overnight. The reaction mixture was filtered through a pad of celite and the resulting filtrate concentrated in vacuo to provide an oil that was used without further purification.

Workup

  1. customThe mixture was evacuated
  2. filtrationThe reaction mixture was filtered through a pad of celite
  3. concentrationthe resulting filtrate concentrated in vacuo
  4. customto provide an oil that
  5. customwas used without further purification

Sources & evidence

ORD record
ord-2f07db67ad7349e493b52810f9eb63dd
Source dataset
uspto-grants-2014_09
Patent number
US08829007B2

Reaction notes

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