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

HRID 1677080Notes

Reaction equation

HRID 1677080 reaction equation
Cl.C(OCC)(=O)C.C(OC([N:15]1[CH:19]([C:20]2[CH:25]=[C:24]([F:26])[C:23]([F:27])=[C:22]([F:28])[CH:21]=2)[CH2:18][CH2:17][C@H:16]1[C@H:29]([OH:31])[CH3:30])=O)(C)(C)C>C(OCC)(=O)C>[F:26][C:24]1[CH:25]=[C:20]([CH:19]2[NH:15][C@H:16]([C@H:29]([OH:31])[CH3:30])[CH2:17][CH2:18]2)[CH:21]=[C:22]([F:28])[C:23]=1[F:27]

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 67373559HCID 67373559, 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

4 N hydrochloric acid/ethyl acetate (26.8 mL) was added to an ethyl acetate (20 mL) solution of (S)-2-((R)-1-hydroxyethyl)-5-(3,4,5-trifluorophenyl)pyrrolidine-1-carboxylic acid t-butyl ester (3.71 g), and stirring was continued for 2 hours at room temperature. The solvent was removed under a vacuum, and 5 N sodium hydroxide solution and dichloromethane were added, and the organic layer was partitioned. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was removed under a vacuum, and the title compound (2.6 g) was obtained. The physical property values are as follows.

Workup

  1. customThe solvent was removed under a vacuum, and 5 N sodium hydroxide solution and dichloromethane
  2. additionwere added
  3. customthe organic layer was partitioned
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. customthe solvent was removed under a vacuum

Sources & evidence

ORD record
ord-c46c5497154147309400159580880258
Source dataset
uspto-grants-2011_08
Patent number
US08008293B2

Reaction notes

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