4-(2-Benzyloxy-ethyl)-2,2,6,6-tetramethyl-morpholine → 2-(2,2,6,6-Tetramethylmorpholino)ethanol

HRID 601559Notes

Reaction equation

HRID 601559 reaction equation
C([O:8][CH2:9][CH2:10][N:11]1[CH2:16][C:15]([CH3:18])([CH3:17])[O:14][C:13]([CH3:20])([CH3:19])[CH2:12]1)C1C=CC=CC=1.[H][H]>CO.[Pd]>[CH3:19][C:13]1([CH3:20])[O:14][C:15]([CH3:17])([CH3:18])[CH2:16][N:11]([CH2:10][CH2:9][OH:8])[CH2:12]1

Participants

5

Reactant 2

HCID 574214984-(2-Benzyloxy-ethyl)-2,2,6,6-tetramethyl-morpholineHCID 178418361HCID 178418361, compound2×

Product 1

HCID 574214992-(2,2,6,6-Tetramethylmorpholino)ethanol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 887MethanolSolvent

Procedure

Dissolve 4-(2-benzyloxy-ethyl)-2,2,6,6-tetramethyl-morpholine (490 mg, 1.77 mmol) MeOH (40 mL). Add to a pressure vessel containing a slurry of 10% Pd/C (100 mg) in MeOH (20 mL). Pressurize with 45 psi hydrogen gas. Monitor the reaction by MS. After 48 h, add another portion of 10% Pd/C (100 mg) and re-pressurize to 45 psi hydrogen. Stir an additional 3 days. Filter the reaction mixture through Celite® eluting with MeOH. Concentrate to give the desired product in quantitative yield. MS (ES+) 188.3 (M+1)+.

Workup

  1. additionAdd to a pressure vessel
  2. customMonitor the reaction by MS
  3. filtrationFilter the reaction mixture through Celite®
  4. washeluting with MeOH
  5. concentrationConcentrate

Sources & evidence

ORD record
ord-2034442e72f0451398eeda3881b4f532
Source dataset
uspto-grants-2011_03
Patent number
US07902356B2

Reaction notes

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