Acetic Anhydride → HCID 67860661, compound

HRID 1655647Notes

Reaction equation

HRID 1655647 reaction equation
[C:1]([O:4][C:5](=[O:7])[CH3:6])(=O)[CH3:2].[OH:8][C@@:9]1([CH3:31])[C@@:26]2([CH3:27])[C@@H:13]([CH2:14][CH2:15][C@@H:16]3[C@@H:25]2[CH2:24][CH2:23][C@@:21]2([CH3:22])[C@H:17]3[C@@H](O)C[C:20]2=[O:28])[CH2:12][C:11](=[O:30])[CH2:10]1>N1C=CC=CC=1.C(OCC)(=O)C>[C:5]([O:4][C@@H:1]1[C@H:17]2[C@H:16]3[C@H:25]([CH2:24][CH2:23][C@:21]2([CH3:22])[C:20](=[O:28])[CH2:2]1)[C@:26]1([CH3:27])[C@H:13]([CH2:12][C:11](=[O:30])[CH2:10][C@:9]1([OH:8])[CH3:31])[CH2:14][CH2:15]3)(=[O:7])[CH3:6]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 67860436HCID 67860436, compound

Product 1

HCID 67860661HCID 67860661, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

20 ml of acetic anhydride is instilled at room temperature in 10.0 g of 1β,15α-dihydroxy-1α-methyl-5α-androstane-3,17-dione in 40 ml of pyridine. The reaction mixture is stirred into ice/water after 2.5 hours. The precipitated product is suctioned off, dissolved in ethyl acetate and washed neutral with water. The crude product is chromatographed on silica gel with a hexane-ethyl acetate gradient. 8.6 g of 15α-acetoxy-1β-hydroxy-1α-methyl-5α-androstane-3,17-dione is obtained. Melting point 170.0° C.

Workup

  1. washwashed neutral with water
  2. customThe crude product is chromatographed on silica gel with a hexane-ethyl acetate gradient

Sources & evidence

ORD record
ord-b2e5af3afdd04087bdbd5b83c0e2680f
Source dataset
uspto-grants-1993_10
Patent number
US05250712

Reaction notes

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