Hydrogen chloride-ethyl acetate → (R)-1-[(S)-5-(3,4,5-trifluorophenyl)pyrrolidine-2-yl]ethanol

HRID 16383Notes

Reaction equation

HRID 16383 reaction equation
C(OC([N:8]1[CH:12]([C:13]2[CH:18]=[C:17]([F:19])[C:16]([F:20])=[C:15]([F:21])[CH:14]=2)[CH2:11][CH2:10][C@@H:9]1[CH:22]([OH:24])[CH3:23])=O)(C)(C)C.Cl.C(OCC)(=O)C>C(OCC)(=O)C>[F:19][C:17]1[CH:18]=[C:13]([CH:12]2[NH:8][C@H:9]([C@H:22]([OH:24])[CH3:23])[CH2:10][CH2:11]2)[CH:14]=[C:15]([F:21])[C:16]=1[F:20]

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 86627818HCID 86627818, compound

Product 1

HCID 67371908(R)-1-[(S)-5-(3,4,5-trifluorophenyl)pyrrolidine-2-yl]ethanolYield 98.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (S)-2-((R)-1-hydroxylethyl-5-(3,4,5-trifluorophenyl)pyrrolidine-1-carboxylic acid t-butyl ester (3.71 g) in ethyl acetate (20 mL) was added 4 N hydrochloric acid/ethyl acetate (26.8 mL), and the resultant solution was stirred at room temperature for 2 hours. Solvent was removed by distillation under reduced pressure, and the resultant product was diluted with 5 N aqueous sodium hydroxide and dichloromethane. The organic layer was partitioned and then dried over anhydrous magnesium sulfate. Solvent was removed by distillation under reduced pressure, to thereby obtain the titled compound (2.6 g). The physical properties of this crude product were as follows.

Workup

  1. customSolvent was removed by distillation under reduced pressure
  2. additionthe resultant product was diluted with 5 N aqueous sodium hydroxide and dichloromethane
  3. customThe organic layer was partitioned
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customSolvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-fecd05bd784c4f9bb8577344bed46972
Source dataset
uspto-grants-2010_06
Patent number
US07737141B2

Reaction notes

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