(Diethylamino)sulfur trifluoride → 5-(3-Fluorooxetan-3-yl)isoindoline
Reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]3(O)[CH2:13][O:12][CH2:11]3)=[CH:7][CH:8]=2)[CH2:3][NH:2]1.C(N(S(F)(F)[F:21])CC)C>C(#N)C.[N+](C)([O-])=O>[F:21][C:10]1([C:6]2[CH:5]=[C:4]3[C:9](=[CH:8][CH:7]=2)[CH2:1][NH:2][CH2:3]3)[CH2:13][O:12][CH2:11]1Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
To 0.58 mmol 3-(2,3-dihydro-1H-isoindol-5-yl)-oxetan-3-ol in 2 ml acetonitrile and 2 ml nitromethane at −60° C. was added 1.15 mmol diethylaminosulfur trifluoride and the mixture was allowed to warm to 0° C. over 30 min. The reaction mixture was re-cooled to −60° C. and quenched by addition of 5 ml saturated aq. sodium carbonate solution. The mixture was warmed to RT and diluted with THF and ethyl acetate, then washed sequentially with water and with brine. The organic phase was separated, dried over sodium sulfate, and concentrated in vacuo to afford the title compound as a brown oil (67% yield). MS (m/e): 194.3 ([M+H]+, 100%).
Workup
- temperatureThe reaction mixture was re-cooled to −60° C.
- customquenched by addition of 5 ml saturated aq. sodium carbonate solution
- temperatureThe mixture was warmed to RT
- additiondiluted with THF and ethyl acetate
- washwashed sequentially with water and with brine
- customThe organic phase was separated
- dry with materialdried over sodium sulfate
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-8867b8345eb146e887096e2e73c51610
- Source dataset
- uspto-grants-2012_05
- Patent number
- US08188139B2
Reaction notes
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