Methanol → Methyl 4-benzyl-3-methyl-5-oxomorpholine-3-carboxylate

HRID 1695999Notes

Reaction equation

HRID 1695999 reaction equation
[CH2:1]([N:8]1[C:13](=[O:14])[CH2:12][O:11][CH2:10][C:9]1([CH3:18])[C:15]([OH:17])=[O:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[CH3:24]O>>[CH2:1]([N:8]1[C:13](=[O:14])[CH2:12][O:11][CH2:10][C:9]1([CH3:18])[C:15]([O:17][CH3:24])=[O:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 672692114-Benzyl-3-methyl-5-oxomorpholine-3-carboxylic acid

Product 1

HCID 67268468Methyl 4-benzyl-3-methyl-5-oxomorpholine-3-carboxylate

Conditions

Temperature
50 °C

Procedure

Dissolve 4-benzyl-3-methyl-5-oxomorpholine-3-carboxylic acid (1 eq) in MeOH (10 volumes) and stir. Add sulfuric acid (3 eq) dropwise. Heat at 50° C. for 24 hours. Cool to room temperature and concentrate. Add EtOAc (25 volumes) wash with water (7 volumes), followed by saturated aqueous NaHCO3 (5 volumes), and then water (7 volumes). Dry the EtOAc layer and concentrated to give methyl 4-benzyl-3-methyl-5-oxomorpholine-3-carboxylate.

Workup

  1. temperatureCool to room temperature
  2. concentrationconcentrate
  3. washAdd EtOAc (25 volumes) wash with water (7 volumes)
  4. dry with materialDry the EtOAc layer
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-13a8524c404346c58035581ab6fd96fb
Source dataset
uspto-grants-2012_04
Patent number
US08163755B2

Reaction notes

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