Ammonium Chloride → [2-(4-Fluorophenyl)-2-hydroxycyclopentyl][(methylethyl)sulfonyl]amine

HRID 2184401Notes

Reaction equation

HRID 2184401 reaction equation
[CH3:1][CH:2]([S:4]([NH:7][CH:8]1[CH2:12][CH2:11][CH2:10][C:9]1=[O:13])(=[O:6])=[O:5])[CH3:3].[F:14][C:15]1[CH:20]=[CH:19][C:18]([Mg]Br)=[CH:17][CH:16]=1.[Cl-].[NH4+]>C1COCC1.O>[F:14][C:15]1[CH:20]=[CH:19][C:18]([C:9]2([OH:13])[CH2:10][CH2:11][CH2:12][CH:8]2[NH:7][S:4]([CH:2]([CH3:1])[CH3:3])(=[O:6])=[O:5])=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 22476614HCID 22476614, compoundHCID 178418676HCID 178418676, compound

Product 1

HCID 9835995[2-(4-Fluorophenyl)-2-hydroxycyclopentyl][(methylethyl)sulfonyl]amine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Scheme IA, step D: Into a flame dried 100 mL 3 neck flask that was fitted with a thermometer and condenser, 2-{[(methylethyl)sulfonyl]amino}cyclopentan-1-one (1.10 g, 5.36 mmol) in THF (25 mL) was added dropwise to 4-fluorophenylmagnesium bromide (3 mL, 2M solution in diethyl ether) while stirring at room temperature under a nitrogen atmosphere and keeping the temperature above 25° C. After the addition was complete, the reaction was refluxed for 2 hours and then stirred overnight at room temperature. In the morning, enough saturated ammonium chloride in water was added to precipitate the salts and the organic layer was decanted off. The remaining salts were washed two times with ether and the combined organic layers were concentrated under reduced vacuum. The resulting material was taken into ethyl acetate, washed once with water, dried over potassium carbonate, filtered, and concentrated under reduced vacuum to yield 930 mg of a dark oil. This isomeric mixture was purified via silica gel chromatography employing the Chromatotron® and using a 4000 micron rotor while eluting with a solvent of hexane/ethyl acetate 7:3 to provide the title compound (787 mg, 49%) as an oil. Ion Spray M.S. 300.1 (M*−1). Calculated for C14H20NO3SF—½H2O: Theory: C, 54.16; H, 6.82; N, 4.51. Found: C, 54.39; H, 6.61; N, 4.69.

Workup

  1. dry with materialScheme IA, step D: Into a flame dried 100 mL 3 neck flask that
  2. customthe temperature above 25° C
  3. additionAfter the addition
  4. temperaturethe reaction was refluxed for 2 hours
  5. stirringstirred overnight at room temperature
  6. customto precipitate the salts
  7. customthe organic layer was decanted off
  8. washThe remaining salts were washed two times with ether
  9. concentrationthe combined organic layers were concentrated under reduced vacuum
  10. washwashed once with water
  11. dry with materialdried over potassium carbonate
  12. filtrationfiltered
  13. concentrationconcentrated under reduced vacuum

Sources & evidence

ORD record
ord-48dc7d95d183466abc3f3348bf2cde4a
Source dataset
uspto-grants-2005_05
Patent number
US06900353B2

Reaction notes

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