Benzyl Bromide → 2-Benzyl-6-(3,3-ethylenedioxypyrrolidin-1-yl)pyridine

HRID 2216370

反応式

HRID 2216370 の反応式
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N:8]2[CH2:12][CH2:11][C:10]3([O:16][CH2:15][CH2:14][O:13]3)[CH2:9]2)[N:3]=1.[CH2:17]([Mg]Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(Br)C1C=CC=CC=1.[Mg]>CC(P(C1C=CC=CC=1)C1C=CC=CC=1)C.C1C=CC(PC2C=CC=CC=2)=CC=1.[Cl-].[Ni].C(OCC)C.O1CCCC1>[CH2:17]([C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N:8]2[CH2:12][CH2:11][C:10]3([O:16][CH2:15][CH2:14][O:13]3)[CH2:9]2)[N:3]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

参加物

8

反応物 4

HCID 7498Benzyl BromideHCID 5462224MagnesiumHCID 219422692-Bromo-6-(3,3-ethylenedioxypyrrolidine-1-yl)pyridineHCID 178419663HCID 178419663、化合物

生成物 1

HCID 219422622-Benzyl-6-(3,3-ethylenedioxypyrrolidin-1-yl)pyridine

試薬・触媒・溶媒 3

HCID 21654969Diphenylphosphane;diphenyl(propan-2-yl)phosphane;nickel;chloride触媒HCID 3283Diethyl Ether溶媒2 回HCID 8028Tetrahydrofuran溶媒

実験手順

A mixture of 6.3 g of 2-bromo-6-(3,3-ethylenedioxypyrrolidin-1-yl)pyridine, 240 mg of 1,3-bis(diphenylphosphino)propanenickel (II) chloride and 20 ml of tetrahydrofuran was stirred in advance under nitrogen atmosphere in an ice bath. To this was added dropwise a diethyl ether solution of benzyl magnesium bromide prepared from 3.4 ml of benzyl bromide, 0.8 g of magnesium and 15 ml of diethyl ether, followed by stirring as it was at room temperature for overnight. The reaction mixture was partitioned between a saturated aqueous ammonium chloride solution and ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and then concentrated. The residue was subjected to silica gel column chromatography with 5–10% ethyl acetate/hexane, to give 6.6 g of the title compound.

後処理

  1. stirringby stirring as it
  2. customThe reaction mixture was partitioned between a saturated aqueous ammonium chloride solution and ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-7efc740474614fa8bb53d2db1bac1da8
出典データセット
uspto-grants-2006_09
特許番号
US07112593B2

関連ノート

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