Sodium periodate → 3-(6-Bromobenzothiazol-2-yl)cyclobutanone

HRID 2103661ノート

反応式

HRID 2103661 の反応式
[Br:1][C:2]1[CH:15]=[CH:14][C:5]2[N:6]=[C:7]([CH:9]3[CH2:12][C:11](=C)[CH2:10]3)[S:8][C:4]=2[CH:3]=1.I([O-])(=O)(=O)=[O:17].[Na+]>C1COCC1.O.[Os](=O)(=O)(=O)=O>[Br:1][C:2]1[CH:15]=[CH:14][C:5]2[N:6]=[C:7]([CH:9]3[CH2:12][C:11](=[O:17])[CH2:10]3)[S:8][C:4]=2[CH:3]=1

参加物

6

反応物 2

HCID 23667635Sodium periodateHCID 67145944HCID 67145944、化合物

生成物 1

HCID 671459253-(6-Bromobenzothiazol-2-yl)cyclobutanone収率 76%

試薬・触媒・溶媒 3

HCID 30318Osmium Tetroxide触媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

The product of Example 1B (931 mg, 3.33 mmole) and osmium tetraoxide (28 mg, cat.) were dissolved in 30 ml THF and 15 ml water. The solution was cooled to 0° C. Sodium periodate (1.5 g, 7.0 mmole) was added in small portions. The mixture was stirred at room temperature overnight. The solution was quenched with water, and extracted three times with dichloromethane. The combined organics were dried over sodium sulfate and concentrated to give the crude product, which was purified by chromatography (20% hexane in dichloromethane) to give the title compound (710 mg, 76%). 1H NMR (500 MHz, CDCl3) δ ppm 8.00 (d, J=1.87 Hz, 1H), 7.84 (d, J=8.74 Hz, 1H), 7.59 (dd, J=8.73, 1.87 Hz, 1H), 3.96-4.10 (m, 1H), 3.54-3.76 (m, 4H). MS: (M+H)+=281/283

後処理

  1. customThe solution was quenched with water
  2. extractionextracted three times with dichloromethane
  3. dry with materialThe combined organics were dried over sodium sulfate
  4. concentrationconcentrated
  5. customto give the crude product, which
  6. customwas purified by chromatography (20% hexane in dichloromethane)

出典と根拠

ORDレコード
ord-ac9682ef78954b4fba549ebcac2d68f6
出典データセット
uspto-grants-2009_08
特許番号
US07576110B2

反応ノート

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