HCID 66935227, compound → HCID 66935220, compound

HRID 1396112Notes

Reaction equation

HRID 1396112 reaction equation
C([NH:8][C:9]1([CH:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:14][NH2:15])[CH2:12][CH2:11][CH2:10]1)C1C=CC=CC=1>CCO.[Pd]>[NH2:8][C:9]1([CH:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:14][NH2:15])[CH2:12][CH2:11][CH2:10]1

Participants

4

Reactant 1

HCID 66935227HCID 66935227, compound

Product 1

HCID 66935220HCID 66935220, compoundYield 92.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 2-[1-(benzylamino)cyclobutyl]-N-(tert-butoxycarbonyl)ethylamine (117 mg, 0.384 mmol) in EtOH (5 mL) was added 10% Pd—C (35 mg) and the mixture was stirred under H2 gas 5 kgf/cm2 at room temperature for 5 h. The mixture was filtered, and the filtrate was concentrated in vacuo. The distillation of the residue gave the title compound as a colorless solid (76.0 mg, 92%). 1H-NMR (400 MHz, DMSO-d6) δ 1.37 (9H, s), 1.49-1.58 (2H, m), 1.62-1.77 (4H, m), 1.82-1.91 (2H, m), 2.92-3.01 (2H, m), 6.78 (1H, t, J=5.5 Hz).

Workup

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

Sources & evidence

ORD record
ord-c202bce7339644dba961df5667a7cbe6
Source dataset
uspto-grants-2014_12
Patent number
US08901112B2

Reaction notes

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