Triethylamine → HCID 57757112, compound

To a stirring solution of 2-cyclohexyl-2-phenyl-ethanol (0.9 g, 0.00441 mole) and triethylamine (0.536 g, 0.0053 mole) in dichloromethane (10 mL) at 0° C. was added methanesulfonyl chloride (0.606 g, 0.0053 mole). The reaction was stirred at RT for 2 h. The reaction mixture was next poured into water, and extracted three times with dichloromethane. The solvent was removed and DMF (10 mL) was added to the residue. NaN3 (0.57 g, 0.0088 mole) was added to the solution and the mixture was then stirred overnight at RT. The reaction mixture was washed with water and extracted three times with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered, and concentrated. The crude product was purified by column chromatography over silica gel (silica gel 60, EM Science) using 20% ethyl acetate:hexane as eluent to afford 0.79 g (78% yield) of the title compound as an oil. 1H-NMR (400 MHz, CDCl3) δ 7.26-7.08 (m, 5H), 3.58 (dd, 1H, J=5.2 Hz), 3.48 (dd, 1H, J=8.8 Hz), 2.53 (q, 1H. J=5.2 Hz), 1.87-0.7 (m, 11H).

1. extractionextracted three times with dichloromethane
2. customThe solvent was removed
3. additionDMF (10 mL) was added to the residue
4. stirringthe mixture was then stirred overnight at RT
5. washThe reaction mixture was washed with water
6. extractionextracted three times with ethyl acetate
7. dry with materialThe combined organic layers were dried over sodium sulfate
8. filtrationfiltered
9. concentrationconcentrated
10. customThe crude product was purified by column chromatography over silica gel (silica gel 60, EM Science)

ORD record

ord-1e66c05306284740a984427b8c1c1b7f

Source dataset

uspto-grants-2008_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07365085B2