Prednisone → 21-Hydroxypregna-1,4-diene-3,11,20-trione

HRID 982532

反応式

HRID 982532 の反応式
C[Si](I)(C)C.O[C@:7]1([C@:28]2([CH3:29])[C@H:14]([C@H:15]3[C@H:25]([C:26](=[O:30])[CH2:27]2)[C@:23]2([CH3:24])[C:18](=[CH:19][C:20](=[O:31])[CH:21]=[CH:22]2)[CH2:17][CH2:16]3)[CH2:13][CH2:12]1)[C:8](=[O:11])[CH2:9][OH:10].S([O-])([O-])=O.[Na+].[Na+]>C(#N)C>[OH:10][CH2:9][C:8](=[O:11])[C@@H:7]1[C@:28]2([CH3:29])[C@H:14]([C@H:15]3[C@H:25]([C:26](=[O:30])[CH2:27]2)[C@:23]2([CH3:24])[C:18](=[CH:19][C:20](=[O:31])[CH:21]=[CH:22]2)[CH2:17][CH2:16]3)[CH2:13][CH2:12]1

参加物

5

反応物 3

HCID 5865PrednisoneHCID 24437Sodium SulfiteHCID 85247Trimethylsilyl iodide

生成物 1

HCID 19183721-Hydroxypregna-1,4-diene-3,11,20-trione

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

Trimethylsilyl iodide (5.12 ml, 7.20 g, 36.0 mmol) is added dropwise to a solution of 17α,21-dihydroxypregna-1,4-diene-3,11,20-trione (3.23 g) in freshly distilled acetonitrile. After 30 min, sodium sulfite solution (5%, 150 ml) is added to the reaction mixture. The mixture is partitioned with chloroform (400 ml). The phases are separated, and the aqueous phases is extracted twice with chloroform. The organic layers are combined, washed with sodium bicarbonate (5%), saline, dried over sodium sulfate and concentrated. The concentrate is flash chromatographed eluting with ethyl acetate/hexane (2.3/1). The appropriate fractions are pooled to give 21-hydroxypregna-1,4-diene-3,11,20-trione as an oil and 17-epi-21-hydroxypregna-1,4-diene-3,11,20-trione as a solid, mp 203-206°.

後処理

  1. customThe mixture is partitioned with chloroform (400 ml)
  2. customThe phases are separated
  3. extractionthe aqueous phases is extracted twice with chloroform
  4. washwashed with sodium bicarbonate (5%), saline
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customchromatographed
  8. washeluting with ethyl acetate/hexane (2.3/1)

出典と根拠

ORDレコード
ord-31802dc1b3444ae58c4fe595a52864dc
出典データセット
uspto-grants-1991_02
特許番号
US04996318

関連ノート

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