Hydrogen chloride-ethyl acetate → (1S)-1-(4-fluorophenyl)-2-(methylamino)ethanol

HRID 1351268Notes

Reaction equation

HRID 1351268 reaction equation
C(O[C:6](=O)[N:7]([CH2:9][C@H:10]([C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=1)[OH:11])C)(C)(C)C.Cl.C(OCC)(=O)C>C(OCC)(=O)C>[F:18][C:15]1[CH:14]=[CH:13][C:12]([C@H:10]([OH:11])[CH2:9][NH:7][CH3:6])=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 69416829(2S)-[2-(4-Fluorophenyl)-2-hydroxyethyl]methylcarbamic acid t-butyl ester

Product 1

HCID 15983834(1S)-1-(4-fluorophenyl)-2-(methylamino)ethanolYield 61.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (2S)-[2-(4-fluorophenyl)-2-hydroxyethyl]methylcarbamic acid t-butyl ester (1.25 g) in ethyl acetate was added dropwise a solution of 4N hydrochloric acid-ethyl acetate (40 mL). The solution was allowed to stand at room temperature for 1 hour. After removing the solvent by evaporation, the solution was alkalinized by addition of an aqueous solution of 5N sodium hydroxide, and saturated with sodium chloride. The solution was extracted with dichloromethane, then washed with saturated sodium chloride water. After drying with anhydrous sodium sulfate, the solvent was removed by evaporation. The resulting solid in a mixed solvent of diethyl ether-hexane was collected by filtration, and the title compound (480 mg) was obtained as a colorless solid. The NMR data matched the racemic mixture described in Preparation Example 17.

Workup

  1. customAfter removing the solvent
  2. customby evaporation
  3. additionthe solution was alkalinized by addition of an aqueous solution of 5N sodium hydroxide
  4. extractionThe solution was extracted with dichloromethane
  5. washwashed with saturated sodium chloride water
  6. dry with materialAfter drying with anhydrous sodium sulfate
  7. customthe solvent was removed by evaporation
  8. filtrationThe resulting solid in a mixed solvent of diethyl ether-hexane was collected by filtration

Sources & evidence

ORD record
ord-6822e5bc4c6e4d9aa11e9575059fdde1
Source dataset
uspto-grants-2007_05
Patent number
US07217723B2

Reaction notes

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