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

HRID 1603346Notes

Reaction equation

HRID 1603346 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

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 tetrahydrofnaran 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.

Workup

  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

Sources & evidence

ORD record
ord-17b3581b087f437786b7e1b80c1d5302
Source dataset
uspto-grants-1999_11
Patent number
US05986115

Reaction notes

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