1-(Trimethylsilyl)pyrrolidin-2-one → HCID 67883823, compound
Reaction equation
[O:1]1[CH:8]2[CH:2]1[CH2:3][CH2:4][O:5][C:6]1[CH:12]=[CH:11][CH:10]=[CH:9][C:7]=12.C[Si](C)(C)[N:15]1[CH2:19][CH2:18][CH2:17][C:16]1=[O:20].O.O.O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[O:20]=[C:16]1[CH2:17][CH2:18][CH2:19][N:15]1[C@@H:8]1[C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[O:5][CH2:4][CH2:3][C@H:2]1[OH:1]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
3.24 g (20 mmol) of 4,5-epoxy-2,3,4,5-tetrahydro-1-benzoxepin and 9.60 g (61 mmol) of N-trimethylsilyl-2-oxo-pyrrolidine are dissolved in 8 ml of dry THF and, while cooling, 6.31 g (20 mmol) of tetrabutylammonium fluoride trihydrate are added in one portion, and the mixture is heated at 100° C. for several hours (TLC check). The mixture is hydrolyzed with ice-water and extracted several times with diethyl ether. The combined diethyl ether extracts are washed with saturated sodium chloride solution and dried over sodium sulfate. After filtration and evaporation of the solvent in vacuo, the residue is crystallized in diisopropyl ether/ethyl acetate. Crystals of melting point 151°-153° C. are obtained.
Workup
- temperaturewhile cooling
- extractionextracted several times with diethyl ether
- washThe combined diethyl ether extracts are washed with saturated sodium chloride solution
- dry with materialdried over sodium sulfate
- filtrationAfter filtration and evaporation of the solvent in vacuo
- customthe residue is crystallized in diisopropyl ether/ethyl acetate
- customCrystals of melting point 151°-153° C. are obtained
Sources & evidence
- ORD record
- ord-9fa850d5e3aa4b0090d554099ca5bc25
- Source dataset
- uspto-grants-1993_03
- Patent number
- US05194442
Reaction notes
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