Methyl iodide → 1-cycloheptylmethyl-4-(((2R)-2-((1R)-3,3-difluorocyclopentyl)-2-hydroxy-2-phenylethanoyl)oxy)-1-methylpiperidinium Iodide
Reaction equation
[F:1][C:2]1([F:32])[CH2:6][CH2:5][C@@H:4]([C@@:7]([OH:31])([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:8]([O:10][CH:11]2[CH2:16][CH2:15][N:14]([CH2:17][CH:18]3[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]3)[CH2:13][CH2:12]2)=[O:9])[CH2:3]1.[CH3:33][I:34]>>[I-:34].[CH:18]1([CH2:17][N+:14]2([CH3:33])[CH2:13][CH2:12][CH:11]([O:10][C:8](=[O:9])[C@:7]([C@@H:4]3[CH2:5][CH2:6][C:2]([F:1])([F:32])[CH2:3]3)([OH:31])[C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH2:16][CH2:15]2)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]1Participants
3
Procedure
A solution formed by dissolving 1-(cycloheptylmethyl)piperidin-4-yl (2R)-((1R)-3,3-difluorocyclopentyl)-2-hydroxy-2-phenylethanoate in 0.3 ml of methyl iodide at room temperature was allowed to stand for 12 hours at the same temperature, and excessive reagent was distilled off under reduced pressure. The diastereomers in the residue were separated on preparative thin layer chromatography (Kieselgel™60F254, Art5744 (Merck), chloroform/methanol=5/1) to provide the title compound respectively as 3.8 mg (low polar substance) and 2.8 mg (high polar substance) of colorless oily substances.
Workup
- customA solution formed
- distillationwas distilled off under reduced pressure
- customThe diastereomers in the residue were separated on preparative thin layer chromatography (Kieselgel™60F254, Art5744 (Merck), chloroform/methanol=5/1)
Sources & evidence
- ORD record
- ord-75e2aa17cdee4428aaf8afbb43a92715
- Source dataset
- uspto-grants-2007_03
- Patent number
- US07192969B2
Reaction notes
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