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

HRID 2103661노트

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HRID 2103661 반응식
[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

참가 물질

6

반응물 2

HCID 23667635Sodium periodateHCID 67145944HCID 67145944, 화합물

생성물 1

HCID 671459253-(6-Bromobenzothiazol-2-yl)cyclobutanone수율 76%

시약·촉매·용매 3

HCID 30318Osmium Tetroxide촉매HCID 962Water용매HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

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

후처리

  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)

출처 및 근거

ORD 기록
ord-ac9682ef78954b4fba549ebcac2d68f6
출처 데이터셋
uspto-grants-2009_08
특허 번호
US07576110B2

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