1-Bromo-2-methylpropane → (-)-3-(2,3-Difluorophenyl)-1-isobutylpyrrolidin-3-OL

HRID 1931827Notes

Reaction equation

HRID 1931827 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]([CH3:25])[CH3:24]>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][CH:23]([CH3:25])[CH3:24])[CH2:10]1

Participants

5

Reactant 3

HCID 65551-Bromo-2-methylpropaneHCID 11430Potassium CarbonateHCID 639883833-(2,3-Difluorophenyl)pyrrolidin-3-ol

Product 1

HCID 25143815(-)-3-(2,3-Difluorophenyl)-1-isobutylpyrrolidin-3-OL

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Preparation according to Example 38: 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-methylpropane (0.32 mL, 2.97 mmol). Stirred 4 h. Purification by flash chromatography on silica gel (ethyl acetate/methanol, 2:1). Yield: 0.16 g. [α]D=−16.1° (methanol). The amine was converted to the oxalic acid salt and recrystallized from ethanol/diethyl ether: M.p. 176° C.; MS m/z (relative intensity, 70 eV) 255 (M+3), 182 (45), 213 (12), 127 (6) 212 (bp).

Workup

  1. customPreparation
  2. customPurification by flash chromatography on silica gel (ethyl acetate/methanol, 2:1)
  3. customrecrystallized from ethanol/diethyl ether

Sources & evidence

ORD record
ord-be680201556340e2b5716bb95db87297
Source dataset
uspto-grants-2012_05
Patent number
US08188301B2

Reaction notes

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