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

HRID 1385615

반응식

HRID 1385615 반응식
[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]

참가 물질

5

반응물 2

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

생성물 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

시약·촉매·용매 1

HCID 2631-Butanol용매

실험 절차

—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).

후처리

  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

출처 및 근거

ORD 기록
ord-857bb3e2f3d84941b89ffecb26dcee83
출처 데이터셋
uspto-grants-2001_07
특허 번호
US06262282B1

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