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

HRID 1650070ノート

反応式

HRID 1650070 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-a21e47c3d1b74ddc976a4cb045c17666
出典データセット
uspto-grants-1990_05
特許番号
US04921638

反応ノート

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