Trifluoroacetic acid → 2-Amino-1-(2-(4-fluorophenyl)oxazol-4-yl)ethanol
Reaction equation
FC(F)(F)C(O)=O.[BH4-].[Na+].[F:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[O:18][CH:19]=[C:20]([CH:22]([OH:25])[C:23]#[N:24])[N:21]=2)=[CH:13][CH:12]=1>C1COCC1>[NH2:24][CH2:23][CH:22]([C:20]1[N:21]=[C:17]([C:14]2[CH:15]=[CH:16][C:11]([F:10])=[CH:12][CH:13]=2)[O:18][CH:19]=1)[OH:25]Participants
Procedure
Trifluoroacetic acid (0.35 mL, 4.60 mmol) was added dropwise to a suspension of NaBH4 (0.174 g, 4.60 mmol) in dry THF (10 mL) at 0° C., followed by addition of 2-(2-(4-fluorophenyl)oxazol-4-yl)-2-hydroxyacetonitrile (0.20 g, 0.92 mmol) also portionwise. The reaction mixture was stirred at room temperature for 8 h, and then concentrated under reduced pressure and diluted with ice-water. The mixture was acidified to pH ˜2 using 1.5N HCl at 0° C. and then heated to 50° C. for 20 min. The solution was basified with aqueous NH4OH solution and the organic product was extracted with CHCl3. The combined extracts were washed with brine and concentrated under reduced pressure to afford 2-amino-1-(2-(4-fluorophenyl)oxazol-4-yl)ethanol (120 mg, crude), which was carried through without further purification. MS (ESI) m/z: Calculated for C11H11FN2O2: 222.08. found: 222.8 (M+H)+.
Workup
- concentrationconcentrated under reduced pressure
- additiondiluted with ice-water
- customat 0° C.
- temperatureheated to 50° C. for 20 min
- extractionthe organic product was extracted with CHCl3
- washThe combined extracts were washed with brine
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-eb9d9be991324421b9dd8bff48e16187
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08901156B2
Reaction notes
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