Sodium Hydroxide → (S)-5-benzyloxymethylmorpholin-3-one
Reaction equation
Br[CH2:2][C:3](Cl)=[O:4].[NH2:6][C@@H:7]([CH2:10][O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:8][OH:9].[OH-].[Na+].C1(C)C=CC=CC=1.C1COCC1>C1(C)C=CC=CC=1>[CH2:12]([O:11][CH2:10][C@@H:7]1[NH:6][C:3](=[O:4])[CH2:2][O:9][CH2:8]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1Participants
Conditions
- Temperature
- 0 °C
Procedure
Bromoacetyl chloride (5.06 mL) was added to a mixed solution of (R)-(+)-2-amino-3-benzyloxy-1-propanol (10 g) in toluene (100 mL) and a 2 N sodium hydroxide solution (100 mL) under ice-cooling. The reaction solution was stirred at 0° C. for 30 minutes and then at 60° C. for one hour. The reaction solution was returned to room temperature. Then, a toluene-THF (1:1) mixed solution was added to the reaction solution, and the organic layer was separated. The resulting organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system) to obtain 1.36 g of the title compound. The property values of the compound are as follows.
Workup
- waitat 60° C. for one hour
- customwas returned to room temperature
- additionwas added to the reaction solution
- customthe organic layer was separated
- dry with materialThe resulting organic layer was dried over anhydrous magnesium sulfate
- concentrationconcentrated under reduced pressure
- customThe residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system)
Sources & evidence
- ORD record
- ord-ca0d11541f174961aa87c913c89a700e
- Source dataset
- uspto-grants-2009_11
- Patent number
- US07618960B2
Reaction notes
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