Water → 7alpha-(5-Chloropentyl)-16alpha-fluoro-estra-1,3,5(10)-triene-3,17alpha-diol

HRID 650353노트

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HRID 650353 반응식
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C@@H:7]1[CH2:24][C:23]2[CH:22]=[C:21]([OH:25])[CH:20]=[CH:19][C:18]=2[C@@H:17]2[C@@H:8]1[C@H:9]1[C@@:13]([CH2:15][CH2:16]2)([CH3:14])[C:12](=[O:26])[C@H:11]([F:27])[CH2:10]1.[H-].C(O[Al](OC(C)(C)C)OC(C)(C)C)(C)(C)C.[Li+].O.S(=O)(=O)(O)O>O1CCCC1>[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C@@H:7]1[CH2:24][C:23]2[CH:22]=[C:21]([OH:25])[CH:20]=[CH:19][C:18]=2[C@@H:17]2[C@@H:8]1[C@H:9]1[C@@:13]([CH2:15][CH2:16]2)([CH3:14])[C@H:12]([OH:26])[C@H:11]([F:27])[CH2:10]1

참가 물질

6

반응물 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 16710494Lithium tri-tert-butoxyaluminohydrideHCID 229418077alpha-(5-Chloropentyl)-16alpha-fluoro-estra-1,3,5(10)-trien-3-ol-17-one

생성물 1

HCID 155422577alpha-(5-Chloropentyl)-16alpha-fluoro-estra-1,3,5(10)-triene-3,17alpha-diol수율 35%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
0 °C

실험 절차

392 mg of 7α-(5-chloropentyl)-16α-fluoro-estra-1,3,5(10)-trien-3-ol-17-one, Example 15d), in 2 ml of anhydrous tetrahydrofuran is dissolved, and 1.1 ml of a 1-molar solution of lithium tri-tert-butoxyaluminum hydride in tetrahydrofuran is added while being cooled in an ice bath. It is allowed to stir for 30 minutes at 0° C., then mixed with water and 8% sulfuric acid until a weakly acidic reaction is achieved, and it is extracted three times with ethyl acetate. The organic phase is washed with saturated sodium chloride solution, dried with sodium sulfate and evaporated to dryness in a vacuum. The crude product is chromatographed on silica gel with hexane/ethyl acetate, whereby 118 mg of 7α-(5-chloropentyl)-16α-fluoro-estra-1,3,5(10)-triene-3,17β-diol and 138 mg of 7α-(5-chloropentyl)-16α-fluoro-estra-1,3,5(10)-triene-3,17α-diol is obtained, both as a solid foam.

후처리

  1. temperaturewhile being cooled in an ice bath
  2. extractionit is extracted three times with ethyl acetate
  3. washThe organic phase is washed with saturated sodium chloride solution
  4. dry with materialdried with sodium sulfate
  5. customevaporated to dryness in a vacuum
  6. customThe crude product is chromatographed on silica gel with hexane/ethyl acetate, whereby 118 mg of 7α-(5-chloropentyl)-16α-fluoro-estra-1,3,5(10)-triene-3,17β-diol

출처 및 근거

ORD 기록
ord-5a37964e38694a109d622912c1434b80
출처 데이터셋
uspto-grants-2001_08
특허 번호
US06271403B1

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