Methyl iodide → HCID 118492098, compound
Reaction equation
[CH3:1][C:2]([S@@:5]([NH:7][C@@H:8]([C:11]1[CH:16]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:14]=[C:13]([CH3:21])[CH:12]=1)[CH:9]=[CH2:10])=[O:6])([CH3:4])[CH3:3].[Li+].[CH3:23][Si]([N-][Si](C)(C)C)(C)C.CI>C1COCC1>[CH3:23][N:7]([C@@H:8]([C:11]1[CH:16]=[C:15]([C:17]([F:19])([F:20])[F:18])[CH:14]=[C:13]([CH3:21])[CH:12]=1)[CH:9]=[CH2:10])[S@:5]([C:2]([CH3:1])([CH3:3])[CH3:4])=[O:6]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -60 °C
Procedure
To a solution of (S)-2-methyl-N-((R)-1-(3-methyl-5-(trifluoromethyl)phenyl)allyl) propane-2-sulfinamide (400 mg, 1.25 mmol) in THF (10 mL) under N2 atmosphere was dropwise added LiHMDS (1.9 ml, 1 M in THF, 1.9 mmol) at −60° C. The reaction was stirred for 30 min at −60° C. followed by addition of MeI (712 mg, 32 mmol). After stirring for another 3 h at room temperature, the reaction was quenched with water at 0° C. and then extracted with EtOAc (2×100 mL). The combined organic layers were dried over anhydrous Na2SO4 and then concentrated under reduced pressure. The residue was purified by silica gel chromatography (PE/EtOAc=5/1 to 2/1) to give the title compound (300 mg, yield: 75%); m/z (ES+): 334 [M+H]+.
Workup
- customat −60° C
- stirringAfter stirring for another 3 h at room temperature
- customthe reaction was quenched with water at 0° C.
- extractionextracted with EtOAc (2×100 mL)
- dry with materialThe combined organic layers were dried over anhydrous Na2SO4
- concentrationconcentrated under reduced pressure
- customThe residue was purified by silica gel chromatography (PE/EtOAc=5/1 to 2/1)
Sources & evidence
- ORD record
- ord-6b12fd0f605d4dac965c1459d7643c4e
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09181259B2
Reaction notes
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