Allyl bromide → (+)-1-Allyl-3-(2,3-difluorophenyl)pyrrolidin-3-OL

HRID 1931829Notes

Reaction equation

HRID 1931829 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][CH:23]=[CH2:24]>C(#N)C>[CH2:24]([N:11]1[CH2:12][CH2:13][C:9]([C:3]2[CH:4]=[CH:5][CH:6]=[C:7]([F:8])[C:2]=2[F:1])([OH:14])[CH2:10]1)[CH:23]=[CH2:22]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 639883833-(2,3-Difluorophenyl)pyrrolidin-3-ol

Product 1

HCID 25143817(+)-1-Allyl-3-(2,3-difluorophenyl)pyrrolidin-3-OL

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Preparation according to Example 8: 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) and 3-bromo-1-propene (0.23 mL, 2.78 mmol). Refluxed for 2 h. Purification by flash chromatography on silica gel (ethyl acetate/methanol, 5:1). Yield: 0.33 g. [α]D=−26.6° (methanol). The amine was converted to the oxalic acid salt and recrystallized from methanol/diisopropyl ether: M.p. 120° C.; MS m/z (relative intensity, 70 eV) (239 (M+, 25), 198 (48), 141 (35), 127 (23), 83 (bp).

Workup

  1. customPreparation
  2. temperatureRefluxed for 2 h
  3. customPurification by flash chromatography on silica gel (ethyl acetate/methanol, 5:1)
  4. customrecrystallized from methanol/diisopropyl ether

Sources & evidence

ORD record
ord-052b8abba57f47058109a4f09c99a01f
Source dataset
uspto-grants-2012_05
Patent number
US08188301B2

Reaction notes

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