Triethylamine → N-Ethyl-N-[(oxiran-2-yl)methyl]aniline

Temperature

0 °C

Methanesulfonyl chloride (2.5 mL, 1.5 eq.) was added to a solution 3-(ethyl-phenyl-amino)-propane-1,2-diol (4.22 g, 21.6 mmol) and triethylamine (9.03 mL, 3.0 eq.) in dichloromethane (20 mL) at −30 to −35° C. and the resulting mixture was stirred and warmed to 0° C. The reaction was quenched by sat. NaHCO3 (30 mL) and the separated aqueous phase was extracted with 2×20 mL CH2Cl2 and 20 mL EtOAc. The combined extracts were dried over Na2SO4, filtered and concentrated. The residue was dissolved in MeOH (30 mL) and treated with NaOMe (2.3 g, 2.0 eq.) at 65-70° C. for 3 h. After cooling to room temperature, the mixture was diluted with sat. NaHCO3 (50 mL) and extracted with 3×30 mL of EtOAc. The combined extracts were dried over Na2SO4, filtered and concentrated and the product was purified by chromatography (10% EtOAc/hexanes) to give ethyl-oxiranylmethyl-phenyl-amine (1.72 g, 45%).

1. customThe reaction was quenched by sat. NaHCO3 (30 mL)
2. extractionthe separated aqueous phase was extracted with 2×20 mL CH2Cl2 and 20 mL EtOAc
3. dry with materialThe combined extracts were dried over Na2SO4
4. filtrationfiltered
5. concentrationconcentrated
6. dissolutionThe residue was dissolved in MeOH (30 mL)
7. temperatureAfter cooling to room temperature
8. extractionextracted with 3×30 mL of EtOAc
9. dry with materialThe combined extracts were dried over Na2SO4
10. filtrationfiltered
11. concentrationconcentrated
12. customthe product was purified by chromatography (10% EtOAc/hexanes)

ORD record

ord-d06f7c3d257840238353f3738c910c42

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08691814B2