HCID 67509562, compound → HCID 67508361, compound

HRID 1770774Notes

Reaction equation

HRID 1770774 reaction equation
C([O:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]1[C:17](=[O:18])[C:16]([CH3:20])([CH3:19])[NH:15][C:14]1([CH3:22])[CH3:21])C1C=CC=CC=1>C(O)C.[Pd]>[OH:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]1[C:17](=[O:18])[C:16]([CH3:20])([CH3:19])[NH:15][C:14]1([CH3:22])[CH3:21]

Participants

4

Reactant 1

HCID 67509562HCID 67509562, compound

Product 1

HCID 67508361HCID 67508361, compoundYield 26.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

3-(4-(benzyloxy)butyl)-2,2,5,5-tetramethylimidazolidin-4-one (3.40 g, 11.2 mmol), was dissolved in ethanol (100 ml), and palladium (10% on carbon, 410 mg, 0.4 mmol) was added to the solution. The flask was purged several times with nitrogen, and then several times with hydrogen. The reaction was stirred at room temperature for 18 hours under hydrogen. The mixture was filtered and purified by silica gel column chromatography (0 to 20% methanol in dichloromethane) to give 628 mg (26%) the title compound. 1H NMR (400 MHz, D2O) δ 3.72 (t, 6.0 Hz, 2H), 3.49 (s, 1H), 3.28-3.20 (m, 2H), 1.76-1.66 (m, 4H), 1.64-1.56 (m, 2H), 1.40 (s, 6H), 1.32 (s, 6H).

Workup

  1. customThe flask was purged several times with nitrogen
  2. filtrationThe mixture was filtered
  3. custompurified by silica gel column chromatography (0 to 20% methanol in dichloromethane)

Sources & evidence

ORD record
ord-2cd1ebeb60444f0b9dc11e2d9dbb3bd1
Source dataset
uspto-grants-2016_02
Patent number
US09248117B2

Reaction notes

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