Iodoethane → 3-(3,4-Difluorophenyl)-1-ethylpyrrolidin-3-ol

HRID 1931803Notes

Reaction equation

HRID 1931803 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-].[Na+].[Na+].I[CH2:22][CH3:23]>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][CH3:23])[CH2:10]2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 10340Sodium CarbonateHCID 635869723-(3,4-Difluorophenyl)pyrrolidin-3-ol

Product 1

HCID 251436623-(3,4-Difluorophenyl)-1-ethylpyrrolidin-3-ol

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Preparation according to Example 8: 3-(3,4-difluorophenyl)pyrrolidin-3-ol (0.38 g, 1.9 mmol), acetonitrile (20 mL), sodium carbonate (0.26 g, 4.75 mmol), iodoethane (0.29 g, 1.9 mmol). Refluxed 2 h. Purification by HPLC on Waters OBD C18, 5 μm (MeOH/33 mM NH3, 35:65 to 50:50). Yield: 0.26 g. The amine was converted to the fumaric acid salt and recrystallized from 2-propanol/diisopropyl ester: M.p. 157-158° C.; MS m/z (relative intensity, 70 eV) 227 (M+, 26), 212 (18), 141 (30), 127 (23), 113 (22), 71 (bp).

Workup

  1. customPreparation
  2. temperatureRefluxed 2 h
  3. customPurification by HPLC on Waters OBD C18, 5 μm (MeOH/33 mM NH3, 35:65 to 50:50)
  4. customrecrystallized from 2-propanol/diisopropyl ester

Sources & evidence

ORD record
ord-218d49eacbd64a8e880d71dabccc465f
Source dataset
uspto-grants-2012_05
Patent number
US08188301B2

Reaction notes

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