Potassium Carbonate → (+)-3-(3,4-Difluorophenyl)-1-propylpyrrolidin-3-OL

HRID 1931818Notes

Reaction equation

HRID 1931818 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]2([OH:14])[CH2:13][CH2:12][NH:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[F:8].C(=O)([O-])[O-].[K+].[K+].I[CH2:22][CH2:23][CH3:24]>C(#N)C>[F:1][C:2]1[CH:3]=[C:4]([C:9]2([OH:14])[CH2:13][CH2:12][N:11]([CH2:22][CH2:23][CH3:24])[CH2:10]2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 336431-IodopropaneHCID 635869723-(3,4-Difluorophenyl)pyrrolidin-3-ol

Product 1

HCID 25145779(+)-3-(3,4-Difluorophenyl)-1-propylpyrrolidin-3-OL

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Preparation according to Example 24: Enantiomer E2 of 3-(3,4-difluorophenyl)-pyrrolidin-3-ol (0.27 g, 1.35 mmol), acetonitrile (3 mL), potassium carbonate (0.279 g, 2.02 mmol) and iodopropane (137 μl, 1.35 mmol). Purification by HPLC on Waters OBD C18, 5 μm (MeOH/33 mM NH3, 45:55 to 60:40). Yield: 0.125 g. [α]D=−21.1° (methanol). The amine was converted to the fumaric acid salt and recrystallized from methanol/diethyl ether/diisopropyl ether: M.p. 128-129° C.; MS m/z (relative intensity, 70 eV) 241 (M+, 9), 212, (bp), 182 (32), 141 (17), 84 (62).

Workup

  1. customPreparation
  2. customPurification by HPLC on Waters OBD C18, 5 μm (MeOH/33 mM NH3, 45:55 to 60:40)
  3. customrecrystallized from methanol/diethyl ether/diisopropyl ether

Sources & evidence

ORD record
ord-fec88ba5d3834043afaf894eae72b543
Source dataset
uspto-grants-2012_05
Patent number
US08188301B2

Reaction notes

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