Potassium Carbonate → HCID 25143818, compound

HRID 1931830Notes

Reaction equation

HRID 1931830 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]1([OH:14])[CH2:13][CH2:12][NH:11][CH2:10]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:22][CH2:23][O:24][CH3:25]>C(#N)C>[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]1([OH:14])[CH2:13][CH2:12][N:11]([CH2:22][CH2:23][O:24][CH3:25])[CH2:10]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 809722-Bromoethyl methyl ether2×HCID 639883833-(2,3-Difluorophenyl)pyrrolidin-3-ol

Product 1

HCID 25143818HCID 25143818, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Preparation according to Example 43: Enantiomer E2 of 3-(2,3-difluorophenyl)-pyrrolidin-3-ol (0.5 g, 2.5 mmol), acetonitrile (20 mL), potassium carbonate (0.69 g, 5 mmol), 1-bromo-2-methoxyethane (0.255 mL, 2.7 mmol). Stirred 1 h at ambient temperature. Addition of 1-bromo-2-methoxyethane (0.05 mL, 0.53 mmol), stirred at 40° C. for 2 min. Purification by flash chromatography on silica gel (ethyl acetate/methanol, 4:1). Yield: 0.32 g. [α]D=−20.8° (methanol). The amine was converted to the oxalic acid salt and recrystallized from methanol/diisopropyl ether: M.p. 146.7° C.; MS m/z (relative intensity, 70 eV) 257 (M+, 2), 212 (bp), 182 (56), 141 (9), 127 (12).

Workup

  1. customPreparation
  2. stirringstirred at 40° C. for 2 min
  3. customPurification by flash chromatography on silica gel (ethyl acetate/methanol, 4:1)
  4. customrecrystallized from methanol/diisopropyl ether

Sources & evidence

ORD record
ord-6ab4fe1107f1480b98013c57c9277766
Source dataset
uspto-grants-2012_05
Patent number
US08188301B2

Reaction notes

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