HCID 178453589, compound → HCID 178453586, compound

HRID 1713884Notes

Reaction equation

HRID 1713884 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C@H:10]1[CH2:15][CH2:14][C@H:13]([C:16]2[CH:21]=[CH:20][C:19]([NH:22]C(=O)OCC3C=CC=CC=3)=[CH:18][CH:17]=2)[CH2:12][CH2:11]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CCO.CCOC(C)=O.[Pd]>[NH2:22][C:19]1[CH:18]=[CH:17][C:16]([C@H:13]2[CH2:12][CH2:11][C@H:10]([CH2:9][NH:8][C:6](=[O:7])[O:5][C:1]([CH3:3])([CH3:2])[CH3:4])[CH2:15][CH2:14]2)=[CH:21][CH:20]=1

Participants

5

Reactant 1

HCID 178453589HCID 178453589, compound

Product 1

HCID 178453586HCID 178453586, compoundYield 92.2%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Benzyl [4-(trans-4-{[(tert-butoxycarbonyl)amino]methyl}cyclohexyl)phenyl]carbamate (0.50 g, 1.14 mmol) in EtOH (10 mL) and EtOAc (10 mL) was hydrogenated over 10% Pd/C (100 mg) at ambient pressure and 40° C. After 2 hours the catalyst was removed by filtration and the solution concentrated in vacuo to leave the title compound (320 mg, 86%) as a white solid; 1H NMR δ 0.95-1.02 (2H, m), 1.25-1.39 (12H, m), 1.73-1.75 (4H, m), 2.22-2.25 (1H, m), 2.80 (2H, t), 4.75 (2H, s), 6.46-6.49 (2H, m), 6.78 (1H, t), 6.85 (2H, d)

Workup

  1. customAfter 2 hours the catalyst was removed by filtration
  2. concentrationthe solution concentrated in vacuo

Sources & evidence

ORD record
ord-af30572120e94ce283dbc0f49f174f70
Source dataset
uspto-grants-2010_09
Patent number
US07795283B2

Reaction notes

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