Sodium Azide → (2R,3R)-3-azido-3-(4-(trifluoromethyl)phenyl)propane-1,2-diol

To a mixture of ((2S,3S)-3-(4-(trifluoromethyl)phenyl)oxiran-2-yl)methanol (15.00 g, 68.8 mmol) in 400 mL ACN was added lithium perchlorate (75.3 mL, 1719 mmol). The reaction mixture was a suspension. After stirring for 15 minutes, sodium azide (12.1 mL, 344 mmol) was added, and the mixture was heated to 65° C. for 24 hours under nitrogen. After the reaction mixture was cooled, the solvent was evaporated under reduced pressure. 500 mL distilled water was added, and the resulting mixture was extracted 3 times (3×400 mL) with diethyl ether. The combined ether layers were directly dried over MgSO4. After removing the solvent, a colorless oil was obtained as the desired product (14.5 g, yield=81%). 1H NMR (400 MHz, CD3OD) δ ppm 3.50-3.56 (m, 1H) 3.58-3.63 (m, 1H) 3.84-3.90 (m, 1H) 4.78 (d, J=6.53 Hz, 1H) 7.62 (d, J=8.03 Hz, 2H) 7.67-7.73 (m, 2H).

1. temperatureAfter the reaction mixture was cooled
2. customthe solvent was evaporated under reduced pressure
3. distillation500 mL distilled water
4. additionwas added
5. extractionthe resulting mixture was extracted 3 times (3×400 mL) with diethyl ether
6. dry with materialThe combined ether layers were directly dried over MgSO4
7. customAfter removing the solvent

ORD 기록

ord-492c2670c60245448c8c38ca64dffb5a

출처 데이터셋

uspto-grants-2009_04

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US07514566B2