Borate → 4-Acetamino-6,7-epoxy-androsta-1,4-diene-3,17-dione

HRID 1440974Notes

Reaction equation

HRID 1440974 reaction equation
[NH:1]([C:5]1[C:22](=[O:23])[CH:21]=[CH:20][C@@:19]2([CH3:24])[C:6]=1[CH:7]=[CH:8][C@@H:9]1[C@@H:18]2[CH2:17][CH2:16][C@@:14]2([CH3:15])[C@H:10]1[CH2:11][CH2:12][C:13]2=[O:25])[C:2]([CH3:4])=[O:3].B([O-])([O-])[O-:27].ClC1C=CC=C(C(OO)=O)C=1.S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+]>C(Cl)Cl>[NH:1]([C:5]1[C:22](=[O:23])[CH:21]=[CH:20][C@@:19]2([CH3:24])[C:6]=1[CH:7]1[O:27][CH:8]1[C@@H:9]1[C@@H:18]2[CH2:17][CH2:16][C@@:14]2([CH3:15])[C@H:10]1[CH2:11][CH2:12][C:13]2=[O:25])[C:2]([CH3:4])=[O:3]

Participants

6

Reactant 4

HCID 26574BorateHCID 70297m-Chloroperbenzoic acidHCID 656671Sodium PyrosulfiteHCID 228594964-Acetamino-androsta-1,4,6-triene-3,17-dione

Product 1

HCID 538134384-Acetamino-6,7-epoxy-androsta-1,4-diene-3,17-dioneYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 4-acetamino-androsta-1,4,6-triene-3,17-dione (3.384 g, 10 mmol) in CH2Cl2 (100 ml) was added borate buffer of pH 8 (50 ml) and then gradually 50% m-chloroperbenzoic acid (6.9 g, 20 mmol) under cooling. The mixture was stirred for 6 h at room temperature until total conversion (TLC monitoring). The mixture was then stirred with 20% sodium metabisulfite solution for 1 h at room temperature. Finally the organic phase was separated, dried and evaporated under vacuum. The residue was submitted to flash chromatography on silica gel with EtOAc thus giving pure title compound in 50% yield (1.772 g).

Workup

  1. customFinally the organic phase was separated
  2. customdried
  3. customevaporated under vacuum

Sources & evidence

ORD record
ord-1061e77345b34ada95bb04e06cf2d3ca
Source dataset
uspto-grants-1996_03
Patent number
US05502044

Reaction notes

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