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

HRID 233652
Notes
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Reaction equation

HRID 233652 reaction equation
[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>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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent
2×

Conditions

Temperature
25 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-bb1b63eb917a472da0acf2011347b65a
Source dataset
uspto-grants-1997_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05593982

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes