Water → HCID 68560345, compound

HRID 1876735Notes

Reaction equation

HRID 1876735 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 (III) 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 free of mother liquor and dried. The 15α-acetoxy-androst-4-ene-3,7-dione is obtained with 88% yield. The reaction is easy-to-carry out, there are no safety and scale-up problems. The 15α-acetoxy compound obtained can be used in the next reaction step without purification.

Workup

  1. filtrationis filtered
  2. washwashed until free of mother liquor
  3. customdried

Sources & evidence

ORD record
ord-4fb3c416d0504fa7b196ed68e81c1f5e
Source dataset
uspto-grants-2012_11
Patent number
US08309712B2

Reaction notes

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