Trifluoroacetic acid → HCID 57516717, compound
Reaction equation
O[CH:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([I:13])=[CH:9][N:8]=2)[C:5](=[O:14])[CH2:4][C:3]1([CH3:16])[CH3:15].FC(F)(F)C(OC(=O)C(F)(F)F)=O.FC(F)(F)C(O)=O.C([SiH](CC)CC)C>C(Cl)Cl>[I:13][C:10]1[CH:11]=[CH:12][C:7]([N:6]2[CH2:2][C:3]([CH3:15])([CH3:16])[CH2:4][C:5]2=[O:14])=[N:8][CH:9]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 22.5 °C
Procedure
(275 mg, 828 μmol) (5RS)-5-Hydroxy-1-(5-iodopyridin-2-yl)-4,4-dimethylpyrrolidin-2-one (Example 13, step 2) was dissolved in CH2Cl2 (2 ml) and trifluoroacetic anhydride (140 μl, 994 μmol, 1.2 equiv.) was added at room temperature. The mixture was stirred for 1 hr at 20-25° C. The solution was evaporated to dryness and the residue was dissolved in trifluoroacetic acid (957 μl, 12.4 mmol, 15 equiv.) and triethylsilane (159 μl, 994 μmol, 1.2 equiv.) was added at room temperature. The mixture was stirred 1 h at room temperature. The reaction mixture was evaporated and extracted with sat. NaHCO3 solution and two times with a small volume of dichloromethane. The crude product was purified by flash chromatography by directly loading the dichloromethane layers onto a silica gel column (20 gr, ethyl acetate/heptane gradient, 0:100 to 100:0). The desired 1-(5-iodopyridin-2-yl)-4,4-dimethylpyrrolidin-2-one (209 mg, 80% yield) was obtained as a white solid, MS: m/e=317.0 (M+H+).
Workup
- customThe solution was evaporated to dryness
- stirringThe mixture was stirred 1 h at room temperature
- customThe reaction mixture was evaporated
- extractionextracted with sat. NaHCO3 solution and two times with a small volume of dichloromethane
- customThe crude product was purified by flash chromatography
Sources & evidence
- ORD record
- ord-0a09abc9da94452ca2ead936e4bc602f
- Source dataset
- uspto-grants-2013_12
- Patent number
- US08618296B2
Reaction notes
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