Trifluoroacetic acid → 5-(4-Bromophenyl)-4-oxa-1-azabicyclo[3.2.1]octane
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([O:20][CH2:21][CH2:22]OS(C3C=CC(C)=CC=3)(=O)=O)[CH2:12][CH2:11][N:10](C(OC(C)(C)C)=O)[CH2:9]2)=[CH:4][CH:3]=1.FC(F)(F)C(O)=O.C([O-])([O-])=O.[K+].[K+]>ClCCl.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]23[CH2:9][N:10]([CH2:11][CH2:12]2)[CH2:22][CH2:21][O:20]3)=[CH:6][CH:7]=1Participants
Conditions
- Temperature
- 40 °C
Procedure
To an ambient solution of Example 54D (0.100 g, 0.186 mmol) in dichloromethane (1 mL) was added trifluoroacetic acid (0.5 ml). The reaction was stirred for 0.5 h, and the solution was then carefully added to a slurry of K2CO3 (3.0 g, 21.7 mmol) 1 h dichloromethane (10 mL). After the evolution of gas ceased, the mixture was heated to 40° C. for 1 h. The mixture was cooled to room temperature and was diluted with water (10 mL). The layers were separated, and the aqueous was extracted with additional dichloromethane (2×10 mL). The combined organic layers were dried with anhydrous Na2SO4, filtered, and concentrated under reduced pressure to give the title product, which was used in the subsequent step without further purification. MS (ESI) m/z 268 [M+H]+.
Workup
- temperatureThe mixture was cooled to room temperature
- customThe layers were separated
- extractionthe aqueous was extracted with additional dichloromethane (2×10 mL)
- dry with materialThe combined organic layers were dried with anhydrous Na2SO4
- filtrationfiltered
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-fcdcc581cdb44e5ab68dfbd06ea2bd8d
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08901152B2
Reaction notes
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