Acetic Acid → 17beta-Cyano-17alpha-hydroxy-16beta-methylandrosta-1,4,9(11)-trien-3-one

HRID 1650070노트

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HRID 1650070 반응식
[CH3:1][C@H:2]1[CH2:7][C@H:6]2[C@H:8]3[C:18](=[CH:19][CH2:20][C@:4]2([CH3:5])[C:3]1=[O:22])[C@:16]1([CH3:17])[C:11](=[CH:12][C:13](=[O:21])[CH:14]=[CH:15]1)[CH2:10][CH2:9]3.[C-:23]#[N:24].[K+].C(O)(=O)C.CC(C)=O.C(Cl)Cl>CO>[C:23]([C@@:3]1([OH:22])[C@@H:2]([CH3:1])[CH2:7][C@H:6]2[C@H:8]3[C:18](=[CH:19][CH2:20][C@:4]12[CH3:5])[C@:16]1([CH3:17])[C:11](=[CH:12][C:13](=[O:21])[CH:14]=[CH:15]1)[CH2:10][CH2:9]3)#[N:24]

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 9032Potassium CyanideHCID 1351855816beta-Methylandrosta-1,4,9(11)-triene-3,17-dioneHCID 21584124Propan-2-one--dichloromethane (1/1)

생성물 1

HCID 1469759117beta-Cyano-17alpha-hydroxy-16beta-methylandrosta-1,4,9(11)-trien-3-one

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

16β-Methylandrosta-1,4,9(11)-triene-3,17-dione (U.S. Pat. No. 3,010,958, 12.0 g) and potassium cyanide (7.909 g) are suspended in methanol (24 ml). The resulting slurry is then treated with glacial acetic acid (3.5 ml) and allowed to stir in a tightly stoppered flask at 20°-25° for 72 hr. TLC (acetone/methylene chloride, 4/96). The reaction mixture is then cooled to 0° and quenched with glacial acetic acid (4.2 ml). The solids are then collected by filtration, triturated with methanol/water (1/1, 3×10 ml) and dried by heating (60°) under reduced pressure (60 mm) to obtain the title compound, m.p. 241°-247.5°; NMR (CD2Cl2) 1.32, 1.42, 5.58, 6.08, 6.30 and 7.25 δ.

후처리

  1. temperatureThe reaction mixture is then cooled to 0°
  2. customquenched with glacial acetic acid (4.2 ml)
  3. filtrationThe solids are then collected by filtration
  4. customtriturated with methanol/water (1/1, 3×10 ml)
  5. customdried
  6. temperatureby heating (60°) under reduced pressure (60 mm)

출처 및 근거

ORD 기록
ord-a21e47c3d1b74ddc976a4cb045c17666
출처 데이터셋
uspto-grants-1990_05
특허 번호
US04921638

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