Cesium carbonate → (R)-1-(4-bromo-3-methyl-phenyl)-4-hydroxy-pyrrolidin-2-one

HRID 1754938ノート

反応式

HRID 1754938 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5](I)=[CH:4][C:3]=1[CH3:9].[OH:10][C@H:11]1[CH2:15][NH:14][C:13](=[O:16])[CH2:12]1.C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C(Cl)(Cl)Cl.[Pd].[Pd].O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:14]2[CH2:15][C@H:11]([OH:10])[CH2:12][C:13]2=[O:16])=[CH:4][C:3]=1[CH3:9]

参加物

8

反応物 4

HCID 10796Cesium carbonateHCID 185505(R)-(+)-4-Hydroxy-2-pyrrolidinoneHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 27355742-Bromo-5-iodotoluene

生成物 1

HCID 66816684(R)-1-(4-bromo-3-methyl-phenyl)-4-hydroxy-pyrrolidin-2-one収率 38.1%

試薬・触媒・溶媒 3

HCID 11029508Palladium, tris[mu-[(1,2-eta:4,5-eta)-(1E,4E)-1,5-diphenyl-1,4-pentadien-3-one]]di-, compd. with trichloromethane (1:1)触媒HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
110 °C

実験手順

A mixture of 2-bromo-5-iodotoluene (500 mg, 1.68 mmol), (R)-4-hydroxy-pyrrolidinone (204 mg, 2.02 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (58.5 mg, 0.101 mmol), tris(dibenzylideneacetone)-dipalladium(0)-chloroform adduct (35.0 mg, 0.034 mmol) and cesium carbonate (769 mg, 2.36 mmol) in 1,4-dioxane (degassed, 5 ml) was stirred at 110° C. overnight in a nitrogen stream. The reaction mixture was treated with H2O and extracted with AcOEt (×2). The organic layers were combined and sequentially washed with H2O and saturated brine, and then dried over Na2SO4 and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (n-hexane/AcOEt) to give (R)-1-(4-bromo-3-methyl-phenyl)-4-hydroxy-pyrrolidin-2-one as a pale brown solid (173 mg, 38%).

後処理

  1. extractionextracted with AcOEt (×2)
  2. washsequentially washed with H2O and saturated brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel chromatography (n-hexane/AcOEt)

出典と根拠

ORDレコード
ord-83cc438b785f4e858558a55f309b7fb2
出典データセット
uspto-grants-2015_10
特許番号
US09169254B2

反応ノート

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