Sodium Bicarbonate → (3beta,20R)-3-[(1-ethoxyethyl)oxy]pregn-5-en-20-ol

HRID 1385615

反応式

HRID 1385615 の反応式
[CH2:1]([O:3][CH:4]([O:6][C@H:7]1[CH2:26][CH2:25][C@@:24]2([CH3:27])[C:9](=[CH:10][CH2:11][C@@H:12]3[C@@H:23]2[CH2:22][CH2:21][C@@:20]2([CH3:28])[C@H:13]3[CH2:14][CH2:15][C@@H:16]2[C:17](=[O:19])[CH3:18])[CH2:8]1)[CH3:5])[CH3:2].C(=O)([O-])O.[Na+]>C(O)CCC>[CH2:1]([O:3][CH:4]([O:6][C@H:7]1[CH2:26][CH2:25][C@@:24]2([CH3:27])[C:9](=[CH:10][CH2:11][C@@H:12]3[C@@H:23]2[CH2:22][CH2:21][C@@:20]2([CH3:28])[C@H:13]3[CH2:14][CH2:15][C@@H:16]2[C@H:17]([OH:19])[CH3:18])[CH2:8]1)[CH3:5])[CH3:2].[CH2:1]([O:3][CH:4]([O:6][C@H:7]1[CH2:26][CH2:25][C@@:24]2([CH3:27])[C:9](=[CH:10][CH2:11][C@@H:12]3[C@@H:23]2[CH2:22][CH2:21][C@@:20]2([CH3:28])[C@H:13]3[CH2:14][CH2:15][C@@H:16]2[C@@H:17]([OH:19])[CH3:18])[CH2:8]1)[CH3:5])[CH3:2]

参加物

5

反応物 2

HCID 516892Sodium BicarbonateHCID 54547839(3beta)-3-[(1-Ethoxyethyl)oxy]pregn-5-en-20-one

生成物 2

HCID 54499379(3beta,20R)-3-[(1-ethoxyethyl)oxy]pregn-5-en-20-olHCID 54499381(3beta,20S)-3-[(1-ethoxyethyl)oxy]pregn-5-en-20-ol

試薬・触媒・溶媒 1

HCID 2631-Butanol溶媒

実験手順

—Sodium (8.98 g) was added in small portions in the course of 2 h to a refluxing solution of (3β)-3-[(1-ethoxyethyl)oxy]pregn-5-en-20-one (20 g) in dry n-butanol (587 ml). Heating was continued for another 2 h; then the reaction mixture was cooled and poured into a saturated aqueous solution of sodium hydrogen carbonate (1.5 l). The product was extracted into ethyl acetate; the combined organic phases were washed with brine, dried over sodium sulfate, and concentrated under reduced pressure. Column chromatography of the crude product afforded (3β,20R)-3-[(1-ethoxyethyl)oxy]pregn-5-en-20-ol (5.08 g) and (3β,20S)-3-[(1-ethoxyethyl)oxy]pregn-5-en-20-ol (compound 3, 7.21 g).

後処理

  1. temperatureHeating
  2. temperaturethen the reaction mixture was cooled
  3. extractionThe product was extracted into ethyl acetate
  4. washthe combined organic phases were washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-857bb3e2f3d84941b89ffecb26dcee83
出典データセット
uspto-grants-2001_07
特許番号
US06262282B1

関連ノート

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