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Tetrahydrofuran → (E)-4-(2-cyclopentyl-1-hydroxymethyl-vinyl)-N-(2-pyridin-2-yl-ethyl)-benzenesulfonamide

HRID 2103624
ノート
印刷プレビュー

反応式

HRID 2103624 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH:20]1(/[CH:25]=[C:26](\B2OC(C)(C)C(C)(C)O2)/[CH2:27][OH:28])[CH2:24][CH2:23][CH2:22][CH2:21]1.[F-].[Cs+].C1COCC1>O1CCOCC1.C1(P([Pd-4](P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH:20]1(/[CH:25]=[C:26](\[C:2]2[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=3)(=[O:10])=[O:9])=[CH:4][CH:3]=2)/[CH2:27][OH:28])[CH2:24][CH2:23][CH2:22][CH2:21]1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 8028TetrahydrofuranHCID 25953Cesium fluorideHCID 35270444-bromo-N-(2-pyridin-2-ylethyl)benzenesulfonamideHCID 67084716(E)-3-cyclopentyl-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-prop-2-en-1-ol

生成物 1

HCID 67084671(E)-4-(2-cyclopentyl-1-hydroxymethyl-vinyl)-N-(2-pyridin-2-yl-ethyl)-benzenesulfonamide収率 49.2%

試薬・触媒・溶媒

2
HCID 178420553HCID 178420553、化合物触媒HCID 312751,4-Dioxane溶媒

実験手順

Heat a suspension of 4-bromo-N-(2-pyridin-2-yl-ethyl)-benzenesulfonamide (1.67 g, 4.89 mmol), (E)-3-cyclopentyl-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-prop-2-en-1-ol (1.60 g, 6.36 mmol), caesium fluoride (2.23 g, 14.7 mmol) and tetrakis(triphenylphosphino)palladium(0) (565 mg, 489 μmol) in 50 mL dioxane to reflux for 2 d and cool to r.t. thereafter. After addition of 50 mL THF filtrate the resulting suspension, wash with dichloromethane and concentrate under reduced pressure. Further purify the resulting brown oil by column chromatography, eluting with a gradient from 100:0 to 0:100 hexanes:ethyl acetate to afford (E)-4-(2-cyclopentyl-1-hydroxymethyl-vinyl)-N-(2-pyridin-2-yl-ethyl)-benzenesulfonamide (929 mg) as a pale yellow oil. MS (m/e): 387 (M+H).

後処理

  1. temperatureHeat
  2. temperatureto reflux for 2 d
  3. washwash with dichloromethane
  4. concentrationconcentrate under reduced pressure
  5. customFurther purify the resulting brown oil by column chromatography
  6. washeluting with a gradient from 100:0 to 0:100 hexanes

出典と根拠

ORDレコード
ord-32af3048a75348b8b7231f209bbace06
出典データセット
uspto-grants-2009_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07576108B2

反応ノート

読み込み中…

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