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

HRID 1182891

반응식

HRID 1182891 반응식
[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

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 887Methanol용매HCID 962Water용매HCID 14798Sodium Hydroxide용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-39899e3e990b4265b77c08a315d184bb
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08664210B2

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