HCID 58134787, compound → HCID 55284400, compound

HRID 444775Notes

Reaction equation

HRID 444775 reaction equation
C([NH:8][C:9]1([CH:13]([CH3:16])[CH2:14][OH:15])[CH2:12][CH2:11][CH2:10]1)C1C=CC=CC=1>CCO.[Pd]>[NH2:8][C:9]1([CH:13]([CH3:16])[CH2:14][OH:15])[CH2:12][CH2:11][CH2:10]1

Participants

4

Reactant 1

HCID 58134787HCID 58134787, compound

Product 1

HCID 55284400HCID 55284400, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

10% Pd—C (700 mg) was added to a solution of 2-[1-(benzylamino)cyclobutyl]propanol (6.81 g, 31.1 mmol) in EtOH (150 mL) and the mixture was stirred under H2 gas 5 kgf/cm2 at room temperature for 6 hours. The mixture was filtered, and the filtrate was concentrated in vacuo. Distillation of the residue gave the title compound as a colorless oil (2.96 g, 74%). 1H-NMR (400 MHz, CDCl3) δ 1.03 (3H, d, J=7.3 Hz), 1.63-1.74 (3H, m), 1.78-1.94 (2H, m), 2.10-2.28 (2H, m), 3.50 (1H, dd, J=11.0 and 4.3 Hz), 3.91 (1H, dd, J=11.0 and 3.1 Hz).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated in vacuo
  3. distillationDistillation of the residue

Sources & evidence

ORD record
ord-04b44b2c7dfe4af5bba9e9e9ab96b306
Source dataset
uspto-grants-2013_07
Patent number
US08476261B2

Reaction notes

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