Acetic Anhydride → (15alpha)-15-(Acetyloxy)androst-4-ene-3,17-dione

HRID 274299Notes

Reaction equation

HRID 274299 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:22])[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]>N1C=CC=CC=1.C(Cl)Cl>[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])[C:4](=[O:22])[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)(=[O:25])[CH3:24]

Participants

5

Reactant 2

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

Product 1

HCID 57023990(15alpha)-15-(Acetyloxy)androst-4-ene-3,17-dione

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

168 g of 15α-hydroxy-4-androstene-3,17-dione in 250 ml of pyridine and 125 ml of acetic anhydride are heated on a steam bath. After 90 minutes, the reaction mixture is stirred into ice/water. The thus-precipitated product is suctioned off, taken up in methylene chloride, washed with water, and dried over sodium sulfate. After recrystallization from ethyl acetate, 120 g of 15α-acetoxy-4-androstene-3,17-dione is obtained, mp 145° C.

Workup

  1. washwashed with water
  2. dry with materialdried over sodium sulfate
  3. customAfter recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-f75258ca317d4ca98f55479aa6368edc
Source dataset
uspto-grants-1995_02
Patent number
US05389624

Reaction notes

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