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

HRID 1359358

反応式

HRID 1359358 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-ethylenedioxypyrrolidine-1-yl)pyridine, 240 mg of 1,3-bis (diphenylphosphino)propanenickel (II) chloride and 20 ml of tetrahydrofuran was stirred in an ice bath in a nitrogen atmosphere. Into the mixture were 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 at room temperature overnight as it was. The reaction solution was partitioned between an aqueous saturated ammonium chloride solution and ethyl acetate. The organic phase was washed with brine, dried over anhydrous magnesium sulfate and then concentrated. The residue was subjected to silica gel column chromatography using 5-10% ethyl acetate/hexane, to give 6.6 g of the target compound.

後処理

  1. stirringby stirring at room temperature overnight as it
  2. customThe reaction solution was partitioned between an aqueous saturated ammonium chloride solution and ethyl acetate
  3. washThe organic phase 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-79150b776aed4c589b81009d95e16a17
出典データセット
uspto-grants-2003_07
特許番号
US06599917B1

関連ノート

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