تفاعل #44624

معادلة التفاعل

toluene

Bromoacetyl chloride

toluene

sodium hydroxide

(R)-(+)-2-amino-3-benzyloxy-1-propanol

→

title compound

(S)-5-benzyloxymethylmorpholin-3-one

المذيبات

THF

ظروف التفاعل

المعالجة

1. 1
   أخرىThe resulting reaction solution
2. 2
   workup.STIRRINGfurther stirred at 60° C. for 1 hr
3. 3
   درجة الحرارةThe reaction solution was cooled to room temperature
4. 4
   workup.ADDITIONwas added
5. 5
   أخرىThe organic layer was separated
6. 6
   تجفيفdried over anhydrous magnesium sulfate
7. 7
   تركيزconcentrated under reduced pressure
8. 8
   أخرىThe residue was purified by silica gel column chromatography (eluting solvent: heptane-ethyl acetate system)

الإجراء التجريبي

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:

المصدر