Aluminium lithium hydride → (3R)-4-Benzyl-3-methylmorpholine

HRID 2357641Notes

Reaction equation

HRID 2357641 reaction equation
[CH2:1]([N:8]1[C@H:13]([CH3:14])[CH2:12][O:11][CH2:10][C:9]1=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH2:1]([N:8]1[CH2:9][CH2:10][O:11][CH2:12][C@H:13]1[CH3:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 51357134HCID 51357134, compound

Product 1

HCID 51357135(3R)-4-Benzyl-3-methylmorpholine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(R)-4-Benzyl-5-methylmorpholin-3-one (5.05 g, 24.6 mmol) was dissolved in THF (12.3 mL) before lithium aluminum hydride (1.87 g, 49.2 mmol) was added and the mixture stirred at RT for 1 h. The reaction mixture was quenched with ethyl acetate before a few drops of ammonium chloride was added. The colorless oil was filtered, washed with dichloromethane, concentrated, and purified by flash chromatography to give the title compound. MS (ES+): 192(M+H)+.

Workup

  1. additionwas added
  2. customThe reaction mixture was quenched with ethyl acetate before a few drops of ammonium chloride
  3. additionwas added
  4. filtrationThe colorless oil was filtered
  5. washwashed with dichloromethane
  6. concentrationconcentrated
  7. custompurified by flash chromatography

Sources & evidence

ORD record
ord-5f408e81e4434b42857c65d9b0c11eec
Source dataset
uspto-grants-2010_07
Patent number
US07759337B2

Reaction notes

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