Ethyl 2-(3-Aminocarbonylmethylphenoxy)-2-methylpropionate → 2-[3-(2-Amino-ethyl)-phenoxy]-2-methyl-propionic acid ethyl ester

Temperature

50 °C

Under nitrogen atmosphere, ethyl 2-(3-aminocarbonylmethylphenoxy)-2-methylpropionate (507 mg, 1.91 mmol) was dissolved in tetrahydrofuran. Subsequently, borane-tetrahydrofuran complex in tetrahydrofuran solution [1M BH3-THF in THF (19.1 mL, 19.1 mmol)] was added thereto, and the mixture was stirred for one hour at 50° C. The reaction mixture was concentrated under reduced pressure, followed by addition of 1M hydrochloric acid at 0° C. and stirring at room temperature. The resultant mixture was made basic with sodium carbonate, followed by extraction with chloroform and drying over sodium sulfate. The reaction mixture was subjected to filtration, concentration under reduced pressure, and purification by silica gel column chromatography (chloroform/methanol=10/1), whereby the target compound was obtained (261.8 mg, 1.04 mmol, 54.5%)

1. concentrationThe reaction mixture was concentrated under reduced pressure
2. additionfollowed by addition of 1M hydrochloric acid at 0° C.
3. stirringstirring at room temperature
4. extractionfollowed by extraction with chloroform
5. dry with materialdrying over sodium sulfate
6. filtrationThe reaction mixture was subjected to filtration, concentration under reduced pressure, and purification by silica gel column chromatography (chloroform/methanol=10/1), whereby the target compound
7. customwas obtained (261.8 mg, 1.04 mmol, 54.5%)

ORD record

ord-570a18dc9cce40299be2642d13efa551

Source dataset

uspto-grants-2003_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06653334B1