HCID 45860617, compound → HCID 59828846, compound

HRID 1191052Notes

Reaction equation

HRID 1191052 reaction equation
C(O)C.O.C(O)(=O)C.[C:9]([NH:13][C:14]([CH2:16][CH2:17][C:18]1[CH:25]=[CH:24][C:21]([C:22]#[N:23])=[CH:20][CH:19]=1)=[O:15])([CH3:12])([CH3:11])[CH3:10]>C(O)C.[Pd]>[C:9]([NH:13][C:14]([CH2:16][CH2:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22][NH2:23])=[CH:20][CH:19]=1)=[O:15])([CH3:12])([CH3:10])[CH3:11]

Participants

5

Reactant 2

HCID 45860617HCID 45860617, compoundHCID 86584229Acetic acid ethanol water

Product 1

HCID 59828846HCID 59828846, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Add 10% Pd/C (Degussa type E101, 62 mg) to a solution of ethanol/water/acetic acid (10:5.6:0.6 mL). Add a solution of 4-[2-(tert-butylcarbamoyl)-ethyl]-benzonitrile (306 mg, 1.33 mmol) in ethanol (3.5 mL) and submit the mixture to hydrogenation at 60 psi overnight. Filter the catalyst through Celite® and concentrate in vacuo to obtain the acetate salt of the title compound. Wash with diethyl ether and filter the solid in vacuo. Add saturated aqueous NaHCO3 and extract twice with EtOAc. Dry the combined organic extracts over MgSO4, filter and concentrate in vacuo to obtain the title compound as a yellow oil (70 mg, 26%). MS (ES+) m/z: 235 (M+H)+.

Workup

  1. customat 60 psi overnight
  2. filtrationFilter the catalyst through Celite®
  3. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-039268950b6b4b0787f4aedb8e770bfb
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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