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

HRID 1069050

반응식

HRID 1069050 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 (compound 3b; 5.08 g) and (3β,20S)-3-[(1-ethoxyethyl)oxy]pregn-5-en-20-ol (compound 3a; 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-2cbab869372440c4a3d3d19b92a9575a
출처 데이터셋
uspto-grants-2001_06
특허 번호
US06251887B1

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