Water → HCID 25102809, compound

HRID 1931800Notes

Reaction equation

HRID 1931800 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]=[C:6]([F:8])[CH:7]=1.C(=O)([O-])[O-].[Na+].[Na+].I[CH2:22][CH3:23].O>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]=[C:6]([F:8])[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 10340Sodium CarbonateHCID 63585886HCID 63585886, compound

Product 1

HCID 25102809HCID 25102809, compoundYield 21.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of 3-(3,5-difluorophenyl)pyrrolidin-3-ol (0.50 g, 2.5 mmol) in acetonitrile (25 mL) was added sodium carbonate (0.34 g, 6.25 mmol) and iodoethane (0.39 g, 2.5 mmol) and the mixture was refluxed for 1 h. Water (50 mL) was added and the aqueous phase was extracted with ethyl acetate (2×50 mL), the combined organic phase was dried (MgSO4) and evaporated. Purification by flash chromatography on silica gel (ethyl acetate/methanol, 1:1) gave the title compound (0.12 g). The amine was converted to the fumaric acid salt and lyophilized from water. MS m/z (relative intensity, 70 eV) 227 (M+, 19), 212 (15), 141 (15), 127 (15), 71 (bp).

Workup

  1. temperaturethe mixture was refluxed for 1 h
  2. extractionthe aqueous phase was extracted with ethyl acetate (2×50 mL)
  3. dry with materialthe combined organic phase was dried (MgSO4)
  4. customevaporated
  5. customPurification by flash chromatography on silica gel (ethyl acetate/methanol, 1:1)

Sources & evidence

ORD record
ord-ace5e61854724013b6ab285272b4da71
Source dataset
uspto-grants-2012_05
Patent number
US08188301B2

Reaction notes

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