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 at 65° C. for 24 hours under nitrogen. The reaction mixture was then cooled, and the solvent was evaporated under reduced pressure. Distilled water (500 mL) 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
- temperatureThe reaction mixture was then cooled
- customthe solvent was evaporated under reduced pressure
- additionDistilled water (500 mL) was 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-6bd8ddc806b14b70a3dc18771c3d2c1e
- Source dataset
- uspto-grants-2011_04
- Patent number
- US07919504B2
Reaction notes
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