Hydrogen Peroxide → Tetrahydro-3'R,5'R-dibenzoyloxy-6'S-methyl-2H-pyrane

HRID 2104227ノート

反応式

HRID 2104227 の反応式
[C:1]([O:9][C@@H:10]1[CH2:16][C@@H:15]([O:17][C:18](=[O:25])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C@H:14]([CH3:26])[O:13][C:11]1=[O:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([BH2-]CCC(C)C)CC(C)C.OO.[OH-].[Na+]>C1COCC1.O>[C:1]([O:9][C@@H:10]1[CH2:16][C@@H:15]([O:17][C:18](=[O:25])[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[C@H:14]([CH3:26])[O:13][CH:11]1[OH:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

7

反応物 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 11473679(2S,3R,5R)-2-methyl-6-oxotetrahydro-2H-pyran-3,5-diyl dibenzoateHCID 131727586Diisoamylborohydride

生成物 1

HCID 16066478Tetrahydro-3'R,5'R-dibenzoyloxy-6'S-methyl-2H-pyrane収率 93.9%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

The compound (IX) (5 g, 14.11 mmol) dissolved in dry THF (15 ml) is added to 0.5M Diisoamylborohydride (127 ml) prepared in the reaction (1). Then, it is stirred for 20 hours at a room temperature. After the reaction is finished, water (3 ml) is added and then stirred for 30 minutes. The reaction mixture is cooled to 0° C., and then 30% H2O2 (15 ml) is added and 3N NaOH is added to maintain the pH 7-8. The solvent THF is vacuum concentrated, and then it is dissolved in CH2Cl2 (100 ml) and washed by water (50 ml). An organic layer is dried using anhydrous MgSO4. The solution is vacuum concentrated, and then the compound (II) (4.72 g, 93.8%, α:β=4.6:1) is isolated using flash column chromatography (toluene/EtOAc, 10:1, v/v).

後処理

  1. stirringstirred for 30 minutes
  2. temperatureThe reaction mixture is cooled to 0° C.
  3. temperatureto maintain the pH 7-8
  4. concentrationconcentrated
  5. dissolutionit is dissolved in CH2Cl2 (100 ml)
  6. washwashed by water (50 ml)
  7. customAn organic layer is dried
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-a6ab7491b1bc4565b276836679538df4
出典データセット
uspto-grants-2009_08
特許番号
US07576225B2

反応ノート

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