(2S,5R)-5-Ethyl-4-(phenylmethyl)-2-morpholinemethanol → [(2S,5R)-5-Ethylmorpholin-2-yl]methanol

HRID 2367550Notes

Reaction equation

HRID 2367550 reaction equation
[CH2:1]([C@H:3]1[N:8](CC2C=CC=CC=2)[CH2:7][C@@H:6]([CH2:16][OH:17])[O:5][CH2:4]1)[CH3:2]>CO.[Pd]>[CH2:1]([C@H:3]1[NH:8][CH2:7][C@@H:6]([CH2:16][OH:17])[O:5][CH2:4]1)[CH3:2]

Participants

4

Reactant 1

HCID 51357958(2S,5R)-5-Ethyl-4-(phenylmethyl)-2-morpholinemethanol

Product 1

HCID 51354034[(2S,5R)-5-Ethylmorpholin-2-yl]methanolYield 100.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

[(2S,5R)-5-Ethyl-4-(phenylmethyl)-2-morpholinyl]methanol (0.5 g, 2.125 mmol) was dissolved in CH3OH (20 mL) and placed under a nitrogen atmosphere. Palladium on carbon (10 wt %, 0.023 g, 0.212 mmol) was added and the flask was flushed with nitrogen and evacuated (3×). Then the reaction was placed under an atmosphere of hydrogen (balloon), and stirred at room temperature overnight. The reaction mixture was filtered through celite and concentrated to afford the title compound (0.309 g) as a colorless oil. LC-MS (ES) m/z=146 [M+H]+.

Workup

  1. customthe flask was flushed with nitrogen
  2. customevacuated (3×)
  3. filtrationThe reaction mixture was filtered through celite
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-12226534b9bb46bcaacad048d0fab5b6
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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