Potassium Hydroxide → (15alpha,16alpha)-15,16-Dihydro-3-methoxy-3′H-cycloprop[15,16]androsta-3,5,15-trien-17-one

HRID 1876736Notes

Reaction equation

HRID 1876736 reaction equation
C(O[C@@H:5]1[C@H:10]2[C@H:11]3[C@H:21]([CH2:22][CH2:23][C@:8]2([CH3:9])[C:7](=[O:26])[CH2:6]1)[C@:19]1([CH3:20])[C:14]([CH:15]=[C:16]([O:24][CH3:25])[CH2:17][CH2:18]1)=[CH:13][CH2:12]3)(=O)C.[I-].[CH3:28][S+](C)(C)=O.[OH-].[K+]>O>[CH2:28]1[C@@H:6]2[C:7](=[O:26])[C@:8]3([CH2:23][CH2:22][C@H:21]4[C@@H:11]([CH2:12][CH:13]=[C:14]5[C@:19]4([CH3:20])[CH2:18][CH2:17][C:16]([O:24][CH3:25])=[CH:15]5)[C@@H:10]3[C@H:5]12)[CH3:9]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 54571005(15alpha)-15-(Acetyloxy)-3-methoxyandrosta-3,5-dien-17-one

Product 1

HCID 14031648(15alpha,16alpha)-15,16-Dihydro-3-methoxy-3′H-cycloprop[15,16]androsta-3,5,15-trien-17-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The 15α-acetoxy-3-methoxy-androsta-3,5-diene-17-one of the general formula (V) is treated with a reagent prepared in situ from trimethylsulfoxonium iodide and potassium hydroxide in a solvent, the reaction mixture is stirred for 6 hours then added to water. The precipitate is filtered off, washed to remove the mother liquor and dried. Finally the 15β,16β-methylene-3-methoxy-androsta-3,5-diene-17-one obtained (a compound of the general formula (VII)) is crystallized from methanol.

Workup

  1. filtrationThe precipitate is filtered off
  2. washwashed
  3. customto remove the mother liquor
  4. customdried

Sources & evidence

ORD record
ord-d69b324726f64ac9a397ee4b3d93a330
Source dataset
uspto-grants-2012_11
Patent number
US08309712B2

Reaction notes

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