2,4-Dimethylphenol → (2R)-1-amino-3-(2,4-dimethylphenoxy)propan-2-ol

Temperature

120 °C

To a solution of (R)—N-(2,3-epoxypropyl)-phthalimide (3.0 g, 14.8 mmol) and 2,4-dimethylphenol (1.6 g, 13.0 mmol) in toluene (30 mL) was added DBU (1.3 mmol) and the resulting mixture was heated at 120° C. for 18 h. The reaction mixture was cooled to 75° C., diluted with isopropanol (50 mL) and treated with hydrazine (4 mL). After stirring the mixture at 80° C. for 4 h, cooled to room temperature and solvents were evaporated in vacuo. The residue was dissolved in aq. NaOH (100 mL, 5 N) and extracted with chloroform (2×100 mL). The combined organic layer was washed with brine (100 mL) and dried over Na2SO4. The solvent was filtered and evaporated in vacuo to afford the desired product as an off-white solid. Yield: 1.7 g, 59% LCMS [M+H]+ 196.1 The product can be recrystallized from isopropyl alcohol.

1. temperatureThe reaction mixture was cooled to 75° C.
2. temperaturecooled to room temperature
3. customsolvents were evaporated in vacuo
4. dissolutionThe residue was dissolved in aq. NaOH (100 mL, 5 N)
5. extractionextracted with chloroform (2×100 mL)
6. washThe combined organic layer was washed with brine (100 mL)
7. dry with materialdried over Na2SO4
8. filtrationThe solvent was filtered
9. customevaporated in vacuo

ORD record

ord-a651e0db704445df9baea92cd607260c

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08686005B2