4-Benzyloxycarbonylamino-cyclohexanecarboxylic acid tert-butyl ester → tert-Butyl 4-aminocyclohexane-1-carboxylate

HRID 2361579Notes

Reaction equation

HRID 2361579 reaction equation
[C:1]([O:5][C:6]([CH:8]1[CH2:13][CH2:12][CH:11]([NH:14]C(OCC2C=CC=CC=2)=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>C1COCC1.[Pd]>[C:1]([O:5][C:6]([CH:8]1[CH2:9][CH2:10][CH:11]([NH2:14])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 538881934-Benzyloxycarbonylamino-cyclohexanecarboxylic acid tert-butyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 18698345tert-Butyl 4-aminocyclohexane-1-carboxylateYield 100.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-benzyloxycarbonylamino-cyclohexanecarboxylic acid tert-butyl ester (3.0 g, 9.009 mmol) in THF (80 mL) is added TEA (0.24 mL, 1.724 mmol) and 10% Pd/C (wet) (420 mg). The mixture stirs under a blanket of hydrogen gas at atmospheric pressure for 12 h. The mixture is then filtered though celite. The celite is washed with MeOH (50 mL). The filtrated is concentrated to afford 1.8 g of 4-amino-cyclohexanecarboxylic acid tert-butyl ester. LC/MS: [M+H]+ 200, Rt=0.39 min (method 6).

Workup

  1. filtrationThe mixture is then filtered though celite
  2. washThe celite is washed with MeOH (50 mL)
  3. concentrationThe filtrated is concentrated

Sources & evidence

ORD record
ord-2d00f2d377a64ca7be09e92204c8a186
Source dataset
uspto-grants-2014_04
Patent number
US08691756B2

Reaction notes

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