Methyl iodide → HCID 69081728, compound

HRID 1785246Notes

Reaction equation

HRID 1785246 reaction equation
[F:1][C:2]1([F:28])[CH2:6][CH2:5][C@@H:4]([C@@:7]([OH:27])([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:8]([O:10][CH:11]2[CH:16]3[CH2:17][CH2:18][CH2:19][CH:12]2[CH2:13][N:14]([CH3:20])[CH2:15]3)=[O:9])[CH2:3]1.[CH3:29][I:30]>>[I-:30].[F:28][C:2]1([F:1])[CH2:6][CH2:5][C@@H:4]([C@@:7]([OH:27])([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:8]([O:10][CH:11]2[CH:12]3[CH2:19][CH2:18][CH2:17][CH:16]2[CH2:15][N+:14]([CH3:29])([CH3:20])[CH2:13]3)=[O:9])[CH2:3]1

Participants

3

Reactant 2

HCID 6328Methyl iodideHCID 20753128HCID 20753128, compound

Product 1

HCID 69081728HCID 69081728, compound

Procedure

Each of the diastereomers of 3-methyl-3-azabicyclo[3.3.1]-non-9-yl (2R)-2-((1R)-3,3-difluorocyclopentyl)-2-hydroxy-2-phenylethanoate was dissolved in 0.5 ml of methyl iodide and heated under reflux for 12 hours. Thereafter the excessive reagent was distilled off under reduced pressure. The residue was purified on a preparative thin layer chromatography (Aluminiumoxide™60F254, Art5713 (Merck), chloroform/methanol=20/1) to provide the title compound whose (9endo**)-body was obtained from the (9endo*)-body, and (9exo**)-body, from the (9exo*)-body, both as colorless, oily substances.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 12 hours
  3. distillationThereafter the excessive reagent was distilled off under reduced pressure
  4. customThe residue was purified on a preparative thin layer chromatography (Aluminiumoxide™60F254, Art5713 (Merck), chloroform/methanol=20/1)

Sources & evidence

ORD record
ord-e1ff75c1b6ee41e5b300884db48fa03a
Source dataset
uspto-grants-2009_03
Patent number
US07504432B2

Reaction notes

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