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

HRID 1992664Notes

Reaction equation

HRID 1992664 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].C[Si](C)(C)[O-].[K+].[ClH:26]>C(OCC)C.O1CCOCC1>[ClH:26].[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

6

Reactant 3

HCID 313Hydrochloric AcidHCID 23668039Potassium trimethylsilanolateHCID 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

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of methyl (3S,4R)-4-(2,4-difluorophenyl)-1-ethylpyrrolidine-3-carboxylate, from preparation 18 (5.9 g, 22 mmol) in diethyl ether (59 mL) at room temperature under dry nitrogen was added potassium trimethylsilanolate (2.36 g, 26 mmol) in a single portion. The resulting mixture was stirred at room temperature under N2 for 3 hours. A solution of 4M hydrogen chloride in dioxane (20 mL) was then added and the resulting mixture was stirred under dry nitrogen at room temperature for 18 hours, and then concentrated in vacuo to afford the title compound as a white solid containing potassium chloride residues (7.0 g).

Workup

  1. stirringthe resulting mixture was stirred under dry nitrogen at room temperature for 18 hours
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0c5d2a6130d04a11888bc74d576ad4d7
Source dataset
uspto-grants-2010_01
Patent number
US07649002B2

Reaction notes

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