Water → HCID 68560345, compound

HRID 2098263Notes

Reaction equation

HRID 2098263 reaction equation
[OH:1][C@@H:2]1[C@H:7]2[C@H:8]3[C@H:18]([CH2:19][CH2:20][C@:5]2([CH3:6])[C:4](=O)[CH2:3]1)[C@:16]1([CH3:17])[C:11](=[CH:12][C:13](=[O:21])[CH2:14][CH2:15]1)[CH2:10][CH2:9]3.[C:23](OC(=O)C)(=[O:25])[CH3:24].[OH2:30]>O1CCCC1.CN(C)C1C=CN=CC=1>[C:23]([O:1][C@@H:2]1[C@H:7]2[C@H:8]3[C@H:18]([CH2:19][CH2:20][C@:5]2([CH3:6])[CH2:4][CH2:3]1)[C@:16]1([CH3:17])[C:11](=[CH:12][C:13](=[O:21])[CH2:14][CH2:15]1)[CH2:10][C:9]3=[O:30])(=[O:25])[CH3:24]

Participants

6

Reactant 3

HCID 962WaterHCID 7918Acetic AnhydrideHCID 1165238315alpha-Hydroxyandrost-4-ene-3,17-dione

Product 1

HCID 68560345HCID 68560345, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

According to this invention the 15α-hydroxy-androst-4-ene-3,17-dione of the formula (II) (Chem. Ind. 1956, 111) preferably is reacted with acetic anhydride in dry tetrahydrofuran in the presence of 4-dimethylaminopyridine below a temperature of 40° C., after the reaction has been completed the reaction mixture is added to water, when the precipitate is dense enough it is filtered, washed until it is free of mother liquor and dried. The 15α-acetoxyandrost-4-ene-3,7-dione of the formula (III) is obtained with 88% yield in a process which is easy to carry out and easy to scale up to any reasonable size. The compound obtained can be used in the next reaction step without further purification.

Workup

  1. filtrationis filtered
  2. washwashed until it
  3. customdried

Sources & evidence

ORD record
ord-6c185f86e6f340669fd349f8549b8641
Source dataset
uspto-grants-2013_05
Patent number
US08450476B2

Reaction notes

Loading…