Sodium Azide → (2R,3R)-3-azido-3-(4-(trifluoromethyl)phenyl)propane-1,2-diol
Reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]2[O:11][C@H:10]2[CH2:12][OH:13])=[CH:5][CH:4]=1.Cl([O-])(=O)(=O)=O.[Li+].[N-:22]=[N+:23]=[N-:24].[Na+]>C(#N)C>[N:22]([C@H:9]([C:6]1[CH:7]=[CH:8][C:3]([C:2]([F:15])([F:14])[F:1])=[CH:4][CH:5]=1)[C@@H:10]([OH:11])[CH2:12][OH:13])=[N+:23]=[N-:24]Participants
Conditions
- Temperature
- 65 °C
Procedure
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).
Workup
- temperatureAfter the reaction mixture was cooled
- customthe solvent was evaporated under reduced pressure
- distillation500 mL distilled water
- additionwas added
- extractionthe resulting mixture was extracted 3 times (3×400 mL) with diethyl ether
- dry with materialThe combined ether layers were directly dried over MgSO4
- customAfter removing the solvent
Sources & evidence
- ORD record
- ord-492c2670c60245448c8c38ca64dffb5a
- Source dataset
- uspto-grants-2009_04
- Patent number
- US07514566B2
Reaction notes
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