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

HRID 1647641
Notes
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Reaction equation

HRID 1647641 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>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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

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 2

HCID 8028
Tetrahydrofuran
Solvent
HCID 21941165TetrahydrofuranatSolvent

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-ba7dc70cb4a84e3b8da68cb796eb47c3
Source dataset
uspto-grants-1995_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05432169

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes