Hydrogen chloride-ethyl acetate → (R)-5-(3,4-difluorophenyl)-3,4-dihydro-2H-pyrrole-2-carboxylic acid ethyl ester

HRID 1677081Notes

Reaction equation

HRID 1677081 reaction equation
Cl.C(OCC)(=O)C.[CH2:8]([O:10][C:11](=[O:33])[C@H:12]([NH:25]C(OC(C)(C)C)=O)[CH2:13][CH2:14][C:15](=O)[C:16]1[CH:21]=[CH:20][C:19]([F:22])=[C:18]([F:23])[CH:17]=1)[CH3:9]>C(OCC)(=O)C>[CH2:8]([O:10][C:11]([C@H:12]1[CH2:13][CH2:14][C:15]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[C:18]([F:23])[CH:17]=2)=[N:25]1)=[O:33])[CH3:9]

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 67373437ethyl (R)-2-tert-butoxycarbonylamino-5-(3,4-difluorophenyl)-5-oxovalerate

Product 1

HCID 67371757(R)-5-(3,4-difluorophenyl)-3,4-dihydro-2H-pyrrole-2-carboxylic acid ethyl esterYield 84.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

4 N hydrochloric acid/ethyl acetate (156 mL) was added to an ethyl acetate (30 mL) solution of (R)-2-t-butoxycarbonylamino-5-oxo-5-(3,4-difluorophenyl) valeric acid ethyl ester (21.2 g), and stirring was continued for 3 hours at room temperature. The solvent was removed under a vacuum, and ethyl acetate and sodium bicarbonate aqueous solution was added to the residue, and the organic layer was partitioned. After washing the organic layer with brine, the resultant was dried over anhydrous magnesium sulfate. The solvent was removed under a vacuum, and the title compound (12.19 g) was obtained. The physical property values were as follows.

Workup

  1. customThe solvent was removed under a vacuum, and ethyl acetate and sodium bicarbonate aqueous solution
  2. additionwas added to the residue
  3. customthe organic layer was partitioned
  4. washAfter washing the organic layer with brine
  5. dry with materialthe resultant was dried over anhydrous magnesium sulfate
  6. customThe solvent was removed under a vacuum

Sources & evidence

ORD record
ord-d8b29653aba7406cb5e39ab129f775bd
Source dataset
uspto-grants-2011_08
Patent number
US08008293B2

Reaction notes

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