N-Boc-(R)-2-(4-benzyloxybenzyl)morpholine → N-BOC-(R)-2-(4-hydroxybenzyl)morpholine

HRID 2252976Notes

Reaction equation

HRID 2252976 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][O:11][C@H:10]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21]CC3C=CC=CC=3)=[CH:17][CH:16]=2)[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]>C(O)C.[Pd]>[C:1]([N:8]1[CH2:13][CH2:12][O:11][C@H:10]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)[CH2:9]1)([O:3][C:4]([CH3:6])([CH3:7])[CH3:5])=[O:2]

Participants

4

Reactant 1

HCID 58689700N-Boc-(R)-2-(4-benzyloxybenzyl)morpholine

Product 1

HCID 58689710N-BOC-(R)-2-(4-hydroxybenzyl)morpholine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
38 °C

Procedure

To a solution of the intermediate (c), N-Boc-(R)-2-(4-benzyloxybenzyl)morpholine (4.92 g, 12.8 mmol) in ethanol (100 mL), was added 10% palladium on charcoal (1.3 g, 1.28 mmol) and the flask flushed with hydrogen. The mixture was stirred at 38° C. for 16 h then filtered through celite and concentrated to afford the product intermediate (b), N-BOC-(R)-2-(4-hydroxybenzyl)morpholine, as a brown oil (3.7 g, 99%).

Workup

  1. customthe flask flushed with hydrogen
  2. filtrationthen filtered through celite
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-6b926d075a944bb78d9158827dd48322
Source dataset
uspto-grants-2008_01
Patent number
US07323466B2

Reaction notes

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