Hydrochloric Acid → (3S*,4R*)-4-(2,4-difluorophenyl)-1-ethylpyrrolidine-3-carboxylic acid hydrochloride

HRID 1992686Notes

Reaction equation

HRID 1992686 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@@H:9]1[CH2:13][N:12]([CH2:14][CH3:15])[CH2:11][C@H:10]1[C:16]([O:18]C)=[O:17].[ClH:20]>>[ClH:20].[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@@H:9]1[CH2:13][N:12]([CH2:14][CH3:15])[CH2:11][C@H:10]1[C:16]([OH:18])=[O:17]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 59130979Methyl (3S*,4R*)-4-(2,4-difluorophenyl)-1-ethylpyrrolidine-3-carboxylate

Product 1

HCID 67211765(3S*,4R*)-4-(2,4-difluorophenyl)-1-ethylpyrrolidine-3-carboxylic acid hydrochloride

Procedure

Concentrated aqueous hydrochloric acid (10 ml) was added to methyl (3S,4R)-4-(2,4-difluorophenyl)-1-ethylpyrrolidine-3-carboxylate from Preparation 76 (500 mg, 1.85 mmol) and the resulting solution was stirred at room temperature for 16 hours. The reaction mixture was then evaporated to dryness in vacuo and the resultant residue was azeotroped with toluene (2×50 ml). This gave the title compound as an off-white foam, 500 mg.

Workup

  1. customThe reaction mixture was then evaporated to dryness in vacuo
  2. customthe resultant residue was azeotroped with toluene (2×50 ml)

Sources & evidence

ORD record
ord-d968bbd6e70042408422effa890c1e1d
Source dataset
uspto-grants-2010_01
Patent number
US07649002B2

Reaction notes

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