1-Benzyl-3-pyrrolidinone → HCID 19935801, compound

HRID 1931858Notes

Reaction equation

HRID 1931858 reaction equation
Br[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([F:9])[CH:3]=1.[Mg].[CH2:11]([N:18]1[CH2:22][CH2:21][C:20](=[O:23])[CH2:19]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>>[CH2:11]([N:18]1[CH2:22][CH2:21][C:20]([C:2]2[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([F:9])[CH:3]=2)([OH:23])[CH2:19]1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

4

Reactant 3

HCID 698901-Benzyl-3-pyrrolidinoneHCID 1363131-Bromo-3,5-difluorobenzeneHCID 5462224Magnesium

Product 1

HCID 19935801HCID 19935801, compound

Procedure

Preparation according to Preparation 1: 1-Bromo-3,5-difluorobenzene (2.0 g, 10.3 mmol), magnesium turnings (0.25 g, 10.3 mmol), 1-benzylpyrrolidin-3-one (1.65 g, 9.3 mmol). Purification using flash chromatography on silica gel (ethyl acetate/isooctane, 1:4 to 1:1). Yield: 0.81 g. MS m/z (rel. intensity, 70 eV) 289 (M+, 2), 198 (26), 133 (32), 132 (23), 91 (bp). The enantiomers were separated by HPLC on Kromasil 5-Cellucoat (heptane/2-propanol/diethyl amine, 99:1:0.1): (+)-enantiomer (0.23 g). [α]D=+28.3° (methanol). MS m/z (rel. intensity, 70 eV) 289 (M+, 5), 198 (48), 133 (48), 132 (37), 91 (bp). (−)-enantiomer (0.35 g). [α]D=−28.1° (methanol). MS m/z (rel. intensity, 70 eV) 289 (M+, 9), 198 (58), 133 (48), 132 (40), 91 (bp).

Workup

  1. customPreparation
  2. customaccording to Preparation 1
  3. customPurification
  4. customThe enantiomers were separated by HPLC on Kromasil 5-Cellucoat (heptane/2-propanol/diethyl amine, 99:1:0.1)

Sources & evidence

ORD record
ord-e57dfecbc93645e8b42758f6a3b13c92
Source dataset
uspto-grants-2012_05
Patent number
US08188301B2

Reaction notes

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