Sulfuric acid magnesium salt (1:1) → 6,7-Dihydro-5H-cyclopenta[b]pyridin-5-ol

HRID 2175898

反応式

HRID 2175898 の反応式
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]2[CH2:7][CH2:8][CH2:9][C:2]=12.[O-:10]S([O-])(=O)=O.[Mg+2].[O-][Mn](=O)(=O)=O.[K+].[BH4-].[Na+]>CC(C)=O.O.CC(O)C>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]2[CH:7]([OH:10])[CH2:8][CH2:9][C:2]=12

参加物

8

反応物 4

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 68292PyrindanHCID 516875Potassium PermanganateHCID 4311764Sodium borohydride

生成物 1

HCID 510640906,7-Dihydro-5H-cyclopenta[b]pyridin-5-ol

試薬・触媒・溶媒 3

HCID 180Acetone溶媒HCID 962Water溶媒2 回HCID 3776Isopropanol溶媒

反応条件

温度
60 °C

実験手順

To a solution of 6,7-dihydro-5H-cyclopenta[b]pyridine (5.0 g, 42 mmol) and MgSO4 (10 g, 84 mmol) in acetone (250 mL) was added a solution of KMnO4 (13 g, 84 mmol) in water (500 mL) at 60 degrees. The mixture was allowed to stir for 30 minutes at 60° C. IPA was slowly added to quench excess KMnO4. The reaction was filtered through a pad of Celite. The filtrate was concentrated under reduced pressure and pumped on a high vacuum pump to ensure complete removal of water. The residue was dissolved in ethanol (200 mL), and cooled with an ice bath. To this solution was slowly added NaBH4 (3.2 g, 84 mmol). When TLC showed complete reduction, water was added to quench excess NaBH4. Ethanol was removed on a rotavapor. The crude material was dissolved in EtOAc, washed with aq. NaHCO3, dried over sodium sulfate, and purified by MPLC (MeOH-DCM: 0-7%). The title compound was collected. LC-MS (IE, m/z): 136 [M+1]+.

後処理

  1. customto quench excess KMnO4
  2. filtrationThe reaction was filtered through a pad of Celite
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customremoval of water
  5. dissolutionThe residue was dissolved in ethanol (200 mL)
  6. temperaturecooled with an ice bath
  7. additionwas added
  8. customto quench excess NaBH4
  9. customEthanol was removed on a rotavapor
  10. dissolutionThe crude material was dissolved in EtOAc
  11. washwashed with aq. NaHCO3
  12. dry with materialdried over sodium sulfate
  13. custompurified by MPLC (MeOH-DCM: 0-7%)
  14. customThe title compound was collected

出典と根拠

ORDレコード
ord-a897840c1150464f9b99acb7c65261e4
出典データセット
uspto-grants-2015_06
特許番号
US09062070B2

関連ノート

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