Toluene → (S)-5-benzyloxymethylmorpholin-3-one

Temperature

0 °C

Bromoacetyl chloride (5.06 mL) was added to a solution mixture of toluene (100 mL) and a 2 N sodium hydroxide aqueous solution (100 mL) of (R)-(+)-2-amino-3-benzyloxy-1-propanol (10 g) under ice-cooling. The resulting reaction solution was stirred at 0° C. for 30 min and then further stirred at 60° C. for 1 hr. The reaction solution was cooled to room temperature, and a solution mixture of toluene and THF (1:1) was added thereto. The organic layer was separated, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: heptane-ethyl acetate system) to give 1.36 g of the title compound. The physical property values of this compound were as follows:

1. customThe resulting reaction solution
2. stirringfurther stirred at 60° C. for 1 hr
3. temperatureThe reaction solution was cooled to room temperature
4. additionwas added
5. customThe organic layer was separated
6. dry with materialdried over anhydrous magnesium sulfate
7. concentrationconcentrated under reduced pressure
8. customThe residue was purified by silica gel column chromatography (eluting solvent: heptane-ethyl acetate system)

ORD record

ord-0de979c1ecc44607a3376da65e857d14

Source dataset

uspto-grants-2010_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07737141B2