Triethylamine → HCID 53785297, compound

HRID 2254627Notes

Reaction equation

HRID 2254627 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:26])[CH2:6]1)[C@:19]1([CH3:20])[C:14](=[C:15]([CH3:25])[C:16](=[O:24])[CH2:17][CH2:18]1)[CH2:13][CH2:12]3)(=[O:3])[CH3:2].[C:27]1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.C(N(CC)CC)C>COC(OC)(C)C.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:26])[CH2:6]1)[C@:19]1([CH3:20])[C:14]([C:15]([CH3:25])=[C:16]([O:24][CH3:27])[CH2:17][CH2:18]1)=[CH:13][CH2:12]3)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 57299791HCID 57299791, compound

Product 1

HCID 53785297HCID 53785297, compoundYield 512.7%

Reagents, catalysts & solvents 2

HCID 64952,2-DimethoxypropaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

5.0 g of 15α-acetoxy-4-methylandrost-4-ene-3,17-dione is stirred at 80° C. in 40 ml of 2,2-dimethoxypropane with 500 mg of pyridinium 4-toluene-sulfonate. After 6 hours, 1 ml of triethylamine is added thereto; the mixture is diluted with ethyl acetate, washed with water, dried, and concentrated under vacuum. The crude product is chromatographed on silica gel containing 2% triethylamine with a hexane-ethyl acetate gradient, thus obtaining 3.8 g of 15α-acetoxy-3-methoxy-4-methylandrosta-3,5-dien-17-one as an oil.

Workup

  1. washwashed with water
  2. customdried
  3. concentrationconcentrated under vacuum
  4. customThe crude product is chromatographed on silica gel containing 2% triethylamine with a hexane-ethyl acetate gradient

Sources & evidence

ORD record
ord-c68ed9b25cca422ba0abf1d429258995
Source dataset
uspto-grants-1993_08
Patent number
US05236912

Reaction notes

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