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Water → 14beta,15beta-Epoxy-17beta-(3-furyl)-5beta-androstan-3alpha-ol

HRID 1647641
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HRID 1647641 반응식
[O:1]1[C@@H:3]2[CH2:4][C@H:5]([C:22]3[CH:26]=[CH:25][O:24][CH:23]=3)[C@:6]3([CH2:8][CH2:9][C@H:10]4[C@H:19]([C@@:2]123)[CH2:18][CH2:17][C@H:16]1[C@:11]4([CH3:21])[CH2:12][CH2:13][C:14](=[O:20])[CH2:15]1)[CH3:7].C(O[Al](OC(C)(C)C)OC(C)(C)C)(C)(C)C.[H-].O>O1CCCC1C([O-])=O.O1CCCC1>[O:24]1[CH:25]=[CH:26][C:22]([C@H:5]2[CH2:4][C@H:3]3[O:1][C@@:2]43[C@H:19]3[C@H:10]([CH2:9][CH2:8][C@:6]24[CH3:7])[C@:11]2([CH3:21])[C@@H:16]([CH2:15][C@H:14]([OH:20])[CH2:13][CH2:12]2)[CH2:17][CH2:18]3)=[CH:23]1
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6

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HCID 962WaterHCID 22484986Tri-tert-butoxyaluminum hydrideHCID 8674878714beta,15beta-Epoxy-17beta-(3-furyl)-5beta-androstan-3-one

생성물 1

HCID 8674878914beta,15beta-Epoxy-17beta-(3-furyl)-5beta-androstan-3alpha-ol수율 95%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매
HCID 21941165
Tetrahydrofuranat
용매

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온도
25 °C

실험 절차

To a solution of 4.5 g of 14β,15β-epoxy-17β-(3-furyl)-5β-androstan-3-one in 30 ml of dry tetrahydrofuran at-78° C, a solution of 9.8 g of tri-tert-butoxyaluminum-hydride in tetrahydrofuran was added dropwise. The mixture was stirred for 20 hrs, then 40 ml of water were added and the temperature raised to 25° C. The aluminum salts were filtered on a celite cake and washed with methanol. The solution was concentrated under reduced pressure and extracted with methylene chloride. The organic layer was dried over sodium sulfate and evaporated to dryness under reduced pressure to give 4.3 g of the title compound (II-b) as a white solid.

후처리

  1. filtrationThe aluminum salts were filtered on a celite cake
  2. washwashed with methanol
  3. concentrationThe solution was concentrated under reduced pressure
  4. extractionextracted with methylene chloride
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. customevaporated to dryness under reduced pressure

출처 및 근거

ORD 기록
ord-ba7dc70cb4a84e3b8da68cb796eb47c3
출처 데이터셋
uspto-grants-1995_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05432169

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