Pyridine → (15alpha)-15-(Acetyloxy)-3-methoxyandrosta-3,5-dien-17-one

HRID 274300Notes

Reaction equation

HRID 274300 reaction equation
[C:1]([O:4][C@@H:5]1[C@H:10]2[C@H:11]3[C@H:21]([CH2:22][CH2:23][C@:8]2([CH3:9])[C:7](=[O:25])[CH2:6]1)[C@:19]1([CH3:20])[C:14](=[CH:15][C:16](=[O:24])[CH2:17][CH2:18]1)[CH2:13][CH2:12]3)(=[O:3])[CH3:2].[CH3:26]OC(OC)(C)C.[NH+]1C=CC=CC=1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.N1C=CC=CC=1>C(OCC)(=O)C>[C:1]([O:4][C@@H:5]1[C@H:10]2[C@H:11]3[C@H:21]([CH2:22][CH2:23][C@:8]2([CH3:9])[C:7](=[O:25])[CH2:6]1)[C@:19]1([CH3:20])[C:14]([CH:15]=[C:16]([O:24][CH3:26])[CH2:17][CH2:18]1)=[CH:13][CH2:12]3)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 1049PyridineHCID 64952,2-DimethoxypropaneHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 57023990(15alpha)-15-(Acetyloxy)androst-4-ene-3,17-dione

Product 1

HCID 54571005(15alpha)-15-(Acetyloxy)-3-methoxyandrosta-3,5-dien-17-one

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

10.0 g of 15α-acetoxy-4-androstene-3,17-dione is stirred under reflux with 60 ml of dimethoxypropane and 1.0 g of pyridinium-4-toluenesulfonate. After 5 hours, 1 ml of pyridine is added, the mixture is diluted with ethyl acetate, washed neutral with water, and dried. The crude product is recrystallized from hexane/acetone. Yield: 9.6 g of 15α-acetoxy-3-methoxyandrosta-3,5-dien-17-one, mp 209° C.

Workup

  1. washwashed neutral with water
  2. customdried
  3. customThe crude product is recrystallized from hexane/acetone

Sources & evidence

ORD record
ord-81c094b18a9541faa1ef8d642a4719eb
Source dataset
uspto-grants-1995_02
Patent number
US05389624

Reaction notes

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