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

HRID 1696000Notes

Reaction equation

HRID 1696000 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-d21651bcb7a1415daf402a3a26ea931d
Source dataset
uspto-grants-2012_04
Patent number
US08163755B2

Reaction notes

Loading…