N-Benzyloxycarbonyl-O-(2-methoxyethoxymethyl)ethanolamine → O-(2-methoxyethoxymethyl)ethanolamine

HRID 361959Notes

Reaction equation

HRID 361959 reaction equation
C(OC([NH:11][CH2:12][CH2:13][O:14][CH2:15][O:16][CH2:17][CH2:18][O:19][CH3:20])=O)C1C=CC=CC=1>C(O)C.[Pd].C(OCC)(=O)C>[CH3:20][O:19][CH2:18][CH2:17][O:16][CH2:15][O:14][CH2:13][CH2:12][NH2:11]

Participants

5

Reactant 1

HCID 54381101N-Benzyloxycarbonyl-O-(2-methoxyethoxymethyl)ethanolamine

Product 1

HCID 19350391O-(2-methoxyethoxymethyl)ethanolamine

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-Benzyloxycarbonyl-O-(2-methoxyethoxymethyl)ethanolamine (6.25 g, 22.0 mmol) was dissolved in ethanol (10 ml) and placed under a blanket of argon. A slurry of 10% palladium on charcoal (1 g) in ethyl acetate was added and hydrogen gas was bubbled through the suspension for 3 hours and then the mixture was placed under hydrogen atmosphere overnight. TLC indicated that some starting material still remained so a further batch ofcatalyst (1 g) was added and hydrogenation was allowed to continue for a further 6 hours, after which all the starting material had been consumed. The catalyst was removed by filtration and the filtrate was used directly in Example 1 h (product volatile).

Workup

  1. customhydrogen gas was bubbled through the suspension for 3 hours
  2. additionwas added
  3. waitto continue for a further 6 hours
  4. customafter which all the starting material had been consumed
  5. customThe catalyst was removed by filtration
  6. customwas used directly in Example 1 h (product volatile)

Sources & evidence

ORD record
ord-86e13b51381a4dc5ad5eeaee299f5b9a
Source dataset
uspto-grants-1999_02
Patent number
US05866717

Reaction notes

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