HCID 9947892, compound → HCID 69789399, compound

HRID 1815777Notes

Reaction equation

HRID 1815777 reaction equation
[Br-].[Br-].[Br-].C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1.[OH:34][CH2:35][C@@H:36]1[CH2:41][CH2:40][C@@H:39]2[C@H:42]3[C@H:51]([CH2:52][CH2:53][C@:37]12[CH3:38])[C:50]1[CH2:49][CH2:48][C:47](=[O:54])[CH2:46][C:45]=1[CH2:44][CH2:43]3>N1C=CC=CC=1>[OH:34][CH2:35][C@@H:36]1[CH2:41][CH2:40][C@@H:39]2[C@H:42]3[C:51]([CH2:52][CH2:53][C@:37]12[CH3:38])=[C:50]1[C:45](=[CH:46][C:47](=[O:54])[CH2:48][CH2:49]1)[CH2:44][CH2:43]3

Participants

4

Reactant 2

HCID 9947892HCID 9947892, compoundHCID 17977687Phenyltrimethylammonium bromide dibromide

Product 1

HCID 69789399HCID 69789399, compoundYield 20.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Phenyltrimethylammonium tribromide (2.28 g) was added in small portions and in 10 min. to a solution of (14β,17α)-17-(hydroxymethyl)estr-5(10)en-3-one (Example 2; 1.75 g) in dry pyridine (47 ml). After 1.5 h stirring at room temperature the mixture was poured into ice-water and the product was extracted into ethyl acetate. The combined organic phases were washed with a saturated aqueous solution of sodium thiosulfate, water, a saturated aqueous solution of sodium hydrogencarbonate and brine, dried over sodium sulfate and concentrated under reduced pressure. Column chromatography provided (14β,17α)-17-(hydroxymethyl)estra-4,9-dien-3-one (0.36 g), [α]D20=−241 (c=1, dioxane).

Workup

  1. extractionthe product was extracted into ethyl acetate
  2. washThe combined organic phases were washed with a saturated aqueous solution of sodium thiosulfate, water
  3. dry with materiala saturated aqueous solution of sodium hydrogencarbonate and brine, dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b294276dd61e4e5ca47da9c02801cc16
Source dataset
uspto-grants-2005_04
Patent number
US06881728B1

Reaction notes

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