2-Bromopropane → HCID 25143960, compound

HRID 1931838Notes

Reaction equation

HRID 1931838 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+].[CH:21](Br)([CH3:23])[CH3:22]>C(#N)C>[F:1][C:2]1[CH:3]=[C:4]([C:9]2([OH:14])[CH2:13][CH2:12][N:11]([CH:21]([CH3:23])[CH3:22])[CH2:10]2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

5

Reactant 3

HCID 63582-BromopropaneHCID 11430Potassium CarbonateHCID 635869723-(3,4-Difluorophenyl)pyrrolidin-3-ol

Product 1

HCID 25143960HCID 25143960, compoundYield 39.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
120 °C

Procedure

In a sealed tube a mixture of 3-(3,4-difluorophenyl)pyrrolidin-3-ol (0.192 g, 0.963 mmol), acetonitrile (3 mL), potassium carbonate (0.133 g, 0.963 mmol) and isopropylbromide (0.118 g, 0.963 mmol) was heated under microwave irradiation at 120° C. for 25 minutes. The mixture was filtrated and evaporated. Purification by flash chromatography on silica gel (ethyl acetate/methanol, 4:1 to 1:1) and by HPLC on Waters OBD C18, 5 μm (MeOH/33 mM NH3, 20:80 to 55:45) gave the title compound (0.092 g). The amine was converted to the fumaric acid salt and recrystallized from ethanol/diethyl ether/diisopropyl ether: M.p. 143-147° C.; MS m/z (relative intensity, 70 eV) 241 (M+, 11), 226 (bp), 182 (46), 85 (53), 84 (31).

Workup

  1. filtrationThe mixture was filtrated
  2. customevaporated
  3. customPurification by flash chromatography on silica gel (ethyl acetate/methanol, 4:1 to 1:1)

Sources & evidence

ORD record
ord-41ea0a2f99b34c23beb3d93f7b63d119
Source dataset
uspto-grants-2012_05
Patent number
US08188301B2

Reaction notes

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