Hydrogen Peroxide → 4beta-Methyl-4alpha,5alpha-epoxy-17beta-hydroxyandrostan-3-one

HRID 1182891

反応式

HRID 1182891 の反応式
[CH3:1][C:2]1[C:18](=[O:19])[CH2:17][CH2:16][C@@:15]2([CH3:20])[C:3]=1[CH2:4][CH2:5][C@@H:6]1[C@@H:14]2[CH2:13][CH2:12][C@@:11]2([CH3:21])[C@H:7]1[CH2:8][CH2:9][C@@H:10]2[OH:22].OO.[O-:25]S([O-])=O.[Na+].[Na+].[Na+].[Cl-]>CO.[OH-].[Na+].O>[CH3:1][C@:2]12[O:25][C@:3]31[C@:15]([CH3:20])([CH2:16][CH2:17][C:18]2=[O:19])[C@@H:14]1[C@H:6]([C@H:7]2[C@@:11]([CH2:12][CH2:13]1)([CH3:21])[C@@H:10]([OH:22])[CH2:9][CH2:8]2)[CH2:5][CH2:4]3

参加物

8

反応物 4

HCID 784Hydrogen PeroxideHCID 5234Sodium ChlorideHCID 24437Sodium SulfiteHCID 2365364-Methyltestosterone

生成物 1

HCID 875533774beta-Methyl-4alpha,5alpha-epoxy-17beta-hydroxyandrostan-3-one収率 25%

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 962Water溶媒HCID 14798Sodium Hydroxide溶媒

実験手順

To a stirred solution of 4-methyltestosterone (500 mg) in MeOH (60 ml) and NaOH 4N (2 ml) at 0° C., 30-32 wt. % H2O2 solution in water (2.0 ml) was added. The suspension was stirred at RT overnight. 10% aqueous Na2SO3 solution (5 ml) was cautiously added dropwise at 0° C. The mixture was saturated with NaCl and extracted three times with EtOAc. The combined organic extracts were dried over Na2SO4, filtered and evaporated to dryness. The crude product was purified by flash chromatography (SiO2, toluene/tert-butyl methyl ether 80/20) to give 4β-methyl-4α,5α-epoxy-17β-hydroxyandrostan-3-one (130 mg, 25%).

後処理

  1. extractionextracted three times with EtOAc
  2. dry with materialThe combined organic extracts were dried over Na2SO4
  3. filtrationfiltered
  4. customevaporated to dryness
  5. customThe crude product was purified by flash chromatography (SiO2, toluene/tert-butyl methyl ether 80/20)

出典と根拠

ORDレコード
ord-39899e3e990b4265b77c08a315d184bb
出典データセット
uspto-grants-2014_03
特許番号
US08664210B2

関連ノート

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