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Hydrochloric Acid → 6alpha,7alpha-Diepoxy-21,21-dimethoxy-20-methylpregn-4-en-3beta-ol

HRID 1708784
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HRID 1708784 반응식
[O:1]1[C:24]2=[C:25]3[C@:20]([CH3:27])([CH2:21][CH2:22][C:23]2=[O:26])[C@@H:19]2[C@H:4]([C@H:5]4[C@:16]([CH3:28])([CH2:17][CH2:18]2)[C@@H:8]([CH:9]([CH3:15])[CH:10]([O:13][CH3:14])[O:11][CH3:12])[CH2:7][CH2:6]4)[C@@H:3]2[O:29][C@:2]123.[BH4-].[Na+].Cl>O1CCCC1.O>[O:1]1[C:24]2=[C:25]3[C@:20]([CH3:27])([CH2:21][CH2:22][C@@H:23]2[OH:26])[C@@H:19]2[C@H:4]([C@H:5]4[C@:16]([CH3:28])([CH2:17][CH2:18]2)[C@@H:8]([CH:9]([CH3:15])[CH:10]([O:13][CH3:14])[O:11][CH3:12])[CH2:7][CH2:6]4)[C@@H:3]2[O:29][C@:2]123
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6

반응물 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 867458216alpha,7alpha-Diepoxy-21,21-dimethoxy-20-methylpregn-4-en-3-one

생성물 1

HCID 867458226alpha,7alpha-Diepoxy-21,21-dimethoxy-20-methylpregn-4-en-3beta-ol수율 62%

시약·촉매·용매 2

HCID 962Water용매
HCID 8028
Tetrahydrofuran
용매

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온도
0 °C

실험 절차

To a solution of 0.402 g (1 mmole) of 1α,2α;6α,7α-diepoxy-21,21-dimethoxy-20-methylpregn-4-en-3-one in 30 ml of tetrahydrofuran was added 38 mg (1 mmole) of sodium borohydride at a temperature of 0° C. and the mixture was stirred at 0° C. for 30 minutes. The reaction mixture was diluted with water and neutralized by adding cold 1N-hydrochloric acid in small portions. From this mixture, the tetrahydrofuran was distilled off under reduced pressure at a temperature not exceeding 20° C. and the residue was diluted with water and extracted with methylene chloride. The extract was washed with aqueous sodium chloride solution and dried over magnesium sulfate. The solvent was then distilled off under reduced pressure. Finally the residue was purified by silica gel chromatography (eluent:ethyl acetate-hexane =1:10, v/v) to recover 0.250 g of 1α,2α;6α,7α-diepoxy-21,21-dimethoxy- 20-methylpregn-4-en-3β-ol (yield: 62%).

후처리

  1. distillationFrom this mixture, the tetrahydrofuran was distilled off under reduced pressure at a temperature not
  2. customexceeding 20° C.
  3. additionthe residue was diluted with water
  4. extractionextracted with methylene chloride
  5. washThe extract was washed with aqueous sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. distillationThe solvent was then distilled off under reduced pressure
  8. customFinally the residue was purified by silica gel chromatography (eluent
  9. customethyl acetate-hexane =1:10, v/v) to recover 0.250 g of 1α,2α

출처 및 근거

ORD 기록
ord-316d61aa6d0d4c47ae3c8b00c5c980f2
출처 데이터셋
uspto-grants-1994_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05359055

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