Water → Methyl 4-benzyl-3-methylmorpholine-3-carboxylate

HRID 2386240Notes

Reaction equation

HRID 2386240 reaction equation
[CH2:1]([N:8]1[C:13](=O)[CH2:12][O:11][CH2:10][C:9]1([CH3:19])[C:15]([O:17][CH3:18])=[O:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.CCOC(C)=O>C1COCC1>[CH2:1]([N:8]1[CH2:13][CH2:12][O:11][CH2:10][C:9]1([CH3:19])[C:15]([O:17][CH3:18])=[O:16])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 8857Ethyl AcetateHCID 67268468Methyl 4-benzyl-3-methyl-5-oxomorpholine-3-carboxylate

Product 1

HCID 67268304Methyl 4-benzyl-3-methylmorpholine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Dissolve methyl 4-benzyl-3-methyl-5-oxomorpholine-3-carboxylate in THF (10 volumes) and cool to 0° C. Add borane dimethylsulfide complex (1.5 eq) and allow to warm to room temperature. Add water (5 volumes) followed by EtOAc (10 volumes). Separate the organic layer, wash with saturated aqueous NaCl, dry over sodium sulfate, filtered, and concentrate to give methyl 4-benzyl-3-methylmorpholine-3-carboxylate.

Workup

  1. temperatureto warm to room temperature
  2. customSeparate the organic layer
  3. washwash with saturated aqueous NaCl
  4. dry with materialdry over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrate

Sources & evidence

ORD record
ord-2a700a83207d44a29efd0240829055a4
Source dataset
uspto-grants-2012_09
Patent number
US08268819B2

Reaction notes

Loading…