Ethanol → (4-Benzyl-3-methylmorpholin-3-yl)methanol

HRID 584229Notes

Reaction equation

HRID 584229 reaction equation
[H-].COCCO[Al+]OCCOC.[Na+].[H-].[CH2:15]([N:22]1[C:27]([CH2:29][OH:30])([CH3:28])[CH2:26][O:25][CH2:24][C:23]1=O)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(O)C.[OH-].[Na+]>C1(C)C=CC=CC=1>[CH2:15]([N:22]1[CH2:23][CH2:24][O:25][CH2:26][C:27]1([CH2:29][OH:30])[CH3:28])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 14798Sodium HydroxideHCID 21584525Sodium bis(2-methoxyethoxy)aluminiumhydrideHCID 223427394-Benzyl-5-(hydroxymethyl)-5-methylmorpholin-3-one

Product 1

HCID 22342862(4-Benzyl-3-methylmorpholin-3-yl)methanolYield 92.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Sodium bis(2-methoxyethoxy)aluminum hydride (3.46 M solution in toluene; 42 ml) was added to a solution of 4-benzyl-5-hydroxymethyl-5-methyl-3-morpholinone (10.77 g) in toluene (100 ml) at 0° C. under nitrogen atmosphere and the whole was stirred at room temperature for 1 hour. Ethanol (20 ml) was added to the mixture at 0° C. and the pH of the mixture was adjusted to 12 by 1N sodium hydroxide solution. The organic layer was separated, added 1N hydrochloric acid and the acidic aqueous layer was separated. This procedure was repeated twice and the combined aqueous layer was made alkaline with 4 M sodium hydroxide solution. It was extracted with ethyl acetate, dried over magnesium sulfate and evaporated in vacuo to give 4-benzyl-3-hydroxymethyl-3-methylmorpholine (9.35 g) as an oil.

Workup

  1. customThe organic layer was separated
  2. additionadded 1N hydrochloric acid
  3. customthe acidic aqueous layer was separated
  4. extractionIt was extracted with ethyl acetate
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-a1e671d68459494080d24db9d0fce367
Source dataset
uspto-grants-2005_08
Patent number
US06924278B2

Reaction notes

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