2-[(Benzyloxy)methyl]-4-tert-butylmorpholine → (4-Tert-butylmorpholin-2-yl)methanol

HRID 2371214Notes

Reaction equation

HRID 2371214 reaction equation
C([O:8][CH2:9][CH:10]1[O:15][CH2:14][CH2:13][N:12]([C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:11]1)C1C=CC=CC=1>[Pd].C(O)C>[C:16]([N:12]1[CH2:13][CH2:14][O:15][CH:10]([CH2:9][OH:8])[CH2:11]1)([CH3:19])([CH3:18])[CH3:17]

Participants

4

Reactant 1

HCID 576569302-[(Benzyloxy)methyl]-4-tert-butylmorpholine

Product 1

HCID 58902595(4-Tert-butylmorpholin-2-yl)methanolYield 102.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 2-[(benzyloxy)methyl]-4-tert-butylmorpholine (268 mg) and 10% palladium on carbon (200 mg) in ethanol (10 mL) was evacuated and purged with hydrogen three times and the left under an atmosphere of hydrogen over the weekend at room temperature. The mixture was filtered through a short pad of celite and the cake was washed with ethanol (10 mL). To the filtrate was added 10% palladium on carbon (200 mg) and the mixture was evacuated and purged with hydrogen three times and the left under an atmosphere of hydrogen for 48 hours. The mixture was filtered through a short pad of celite and the cake was washed with ethanol. The filtrate was concentrated at reduced pressure to give the title compound as a colourless oil (180 mg).

Workup

  1. customwas evacuated
  2. custompurged with hydrogen three times
  3. waitthe left under an atmosphere of hydrogen over the weekend at room temperature
  4. filtrationThe mixture was filtered through a short pad of celite
  5. washthe cake was washed with ethanol (10 mL)
  6. additionTo the filtrate was added 10% palladium on carbon (200 mg)
  7. customthe mixture was evacuated
  8. custompurged with hydrogen three times
  9. filtrationThe mixture was filtered through a short pad of celite
  10. washthe cake was washed with ethanol
  11. concentrationThe filtrate was concentrated at reduced pressure

Sources & evidence

ORD record
ord-3e85e191d3e043f08e3cb8400c0e821a
Source dataset
uspto-grants-2014_04
Patent number
US08710224B2

Reaction notes

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