2-Methyl-2-butene → Epristeride

HRID 862302Notes

Reaction equation

HRID 862302 reaction equation
[OH2:1].O.P([O-])([O-])([O-])=O.[Na+].[Na+].[Na+].Cl([O-])=O.[Na+].CC(=CC)C.[C:20]([NH:24][C:25]([C@H:27]1[CH2:32][CH2:31][C@H:30]2[C@H:33]3[C@H:43]([CH2:44][CH2:45][C@:28]12[CH3:29])[C@:41]1([CH3:42])[C:36]([CH:37]=[C:38]([CH:46]=[O:47])[CH2:39][CH2:40]1)=[CH:35][CH2:34]3)=[O:26])([CH3:23])([CH3:22])[CH3:21]>O.C(O)(C)(C)C>[C:20]([NH:24][C:25]([C@H:27]1[CH2:32][CH2:31][C@H:30]2[C@H:33]3[C@H:43]([CH2:44][CH2:45][C@:28]12[CH3:29])[C@:41]1([CH3:42])[C:36]([CH:37]=[C:38]([C:46]([OH:1])=[O:47])[CH2:39][CH2:40]1)=[CH:35][CH2:34]3)=[O:26])([CH3:21])([CH3:22])[CH3:23]

Participants

7

Reactant 4

HCID 105532-Methyl-2-buteneHCID 18623014Trisodium;phosphate;dihydrateHCID 23668197Sodium ChloriteHCID 86749645N-t-Butyl-3-formylandrosta-3,5-diene-17beta-carboxamide

Product 1

HCID 68741Epristeride

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

600 mg of sodium phosphate dihydrate and 1.2 g of sodium chlorite were added, in that order, at room temperature to a mixture of 7.5 ml of t-butanol, 2.0 m of water and 1 ml of 2-methyl-2-butene containing 400 mg of N-t-butyl-3-formylandrosta-3,5-diene-17β-carboxamide (prepared as described in Preparation 6). The reaction mixture was then stirred for 15 minutes. At the end of this time, the reaction mixture was quenched by pouring it into a ice-cooled aqueous solution of sodium thiosulfate; it was then made acidic by the addition of 1N aqueous hydrochloric acid, and extracted with ethyl acetate three times. The combined organic extracts were washed with water and with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and concentrated by evaporation under reduced pressure. The resulting residue was crystallized by the addition of diethyl ether, to give 225 mg of the title compound.

Workup

  1. customAt the end of this time, the reaction mixture was quenched
  2. additionby pouring it into a ice-
  3. temperaturecooled aqueous solution of sodium thiosulfate
  4. additionmade acidic by the addition of 1N aqueous hydrochloric acid
  5. extractionextracted with ethyl acetate three times
  6. washThe combined organic extracts were washed with water and with a saturated aqueous solution of sodium chloride
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated by evaporation under reduced pressure
  9. customThe resulting residue was crystallized by the addition of diethyl ether

Sources & evidence

ORD record
ord-cf25e25c08d64245b23ff5626f7f9ae2
Source dataset
uspto-grants-1998_02
Patent number
US05717088

Reaction notes

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