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

HRID 2047507Notes

Reaction equation

HRID 2047507 reaction equation
[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

Participants

6

Reactant 2

HCID 23667635Sodium periodateHCID 67145944HCID 67145944, compound

Product 1

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

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

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

Workup

  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)

Sources & evidence

ORD record
ord-e3e94b40bc0748c6b4691a790debd718
Source dataset
uspto-grants-2013_11
Patent number
US08592467B2

Reaction notes

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