Diisopropylethylamine → 5-(4-Methylphenyl)-1,3-oxazolidin-2-one

Temperature

0 °C

Diisopropylethylamine (181 mg, 244 μL, 1.40 mmol) and triphosgene (138 mg, 0.466 mmol) were added successively to a stirred solution of 2-amino-1-(4-methylphenyl)ethanol (35.2 mg, 0.233 mmol) in dry CH2Cl2 (22 mL) at 0° C. under N2. The reaction was stirred at 0° C. for 1 h then concentrated in vacuo to a volume of about 5 mL. The mixture was diluted with water (50 mL) and extracted with EtOAc (3×50 mL). The combined organic extracts were dried (Na2SO4) and concentrated in vacuo to give the crude product. This was purified by flash chromatography (Si, 12×160 mm, 0-80% EtOAc in hexanes gradient) to afford 5-(4-methylphenyl)-1,3-oxazolidin-2-one. Rf=0.41 (50% EtOAc/hexanes). LCMS calc.=178.08; found=178.1 (M+1)+. 1H NMR (CDCl3, 500 MHz) δ 7.25 (d, J=7.4 Hz, 2H), 7.19 (d, J=7.4 Hz, 2H), 6.69 (br s, 1H), 5.55 (t, J=7.8 Hz, 1H), 3.93 (t, J=8.6 Hz, 1H), 3.52 (t, J=8.1 Hz, 1H), 2.35 (s, 3H).

1. concentrationthen concentrated in vacuo to a volume of about 5 mL
2. additionThe mixture was diluted with water (50 mL)
3. extractionextracted with EtOAc (3×50 mL)
4. dry with materialThe combined organic extracts were dried (Na2SO4)
5. concentrationconcentrated in vacuo
6. customto give the crude product
7. customThis was purified by flash chromatography (Si, 12×160 mm, 0-80% EtOAc in hexanes gradient)

ORD record

ord-3976ecf3f55444a19f52db3da634f1bd

Source dataset

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08735435B2