Sulfuric Acid → (3beta,5beta,15alpha,16alpha)-15,16-Dihydro-3,5-dihydroxy-3'H-cycloprop(15,16)androsta-6,15-dien-17-one

HRID 1649466ノート

反応式

HRID 1649466 の反応式
[OH:1][C@@:2]12[CH2:19][C@@H:18]([O:20]C(=O)C(C)(C)C)[CH2:17][CH2:16][C@:15]1([CH3:27])[C@@H:14]1[C@H:5]([C@H:6]3[C@@:10]([CH2:12][CH2:13]1)([CH3:11])[C:9](=[O:28])[C@H:8]1[CH2:29][C@@H:7]31)[CH:4]=[CH:3]2.[OH-].[K+].Cl([O-])(=O)(=O)=O.[Na+].S(=O)(=O)(O)O>O1CCCC1.O.CO>[OH:20][C@H:18]1[CH2:17][CH2:16][C@@:15]2([CH3:27])[C@:2]([OH:1])([CH:3]=[CH:4][C@@H:5]3[C@@H:14]2[CH2:13][CH2:12][C@@:10]2([CH3:11])[C@H:6]3[C@@H:7]3[CH2:29][C@@H:8]3[C:9]2=[O:28])[CH2:19]1

参加物

8

反応物 4

HCID 1118Sulfuric AcidHCID 14797Potassium HydroxideHCID 522606Sodium PerchlorateHCID 130759725-Hydroxy-15 beta,16 beta-methylene-3 beta-pivaloyloxy-5 beta-androst-6-en-17-one

生成物 1

HCID 13075974(3beta,5beta,15alpha,16alpha)-15,16-Dihydro-3,5-dihydroxy-3'H-cycloprop(15,16)androsta-6,15-dien-17-one収率 94.3%

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

134 g of 5-hydroxy-15β,16β-methylene-3β-pivaloyloxy-5β-androst-6-en-17-one is dissolved in 1,340 ml of tetrahydrofuran and 670 ml of methanol and combined in succession with 40 g of pulverized potassium hyroxide and 13 g of sodium perchlorate. After 2.5 hours, the mixture is stirred into 8 l of water, neutralized with 20% sulfuric acid, and the thus-precipitated solid is filtered off. After dissolving the solid in methylene chloride and drying same with sodium sulfate, it is concentrated under vacuum. By trituration of the resultant solid with ethyl acetate, 99.8 g of 3β,5-dihydroxy-15β,16β-methylene-5β-androst-6-en-17-one is produced, mp 198° C.

後処理

  1. filtrationthe thus-precipitated solid is filtered off
  2. dissolutionAfter dissolving the solid in methylene chloride
  3. dry with materialdrying same with sodium sulfate, it
  4. concentrationis concentrated under vacuum

出典と根拠

ORDレコード
ord-6808f4c1f2b34c58b98e69b69bd4e1a8
出典データセット
uspto-grants-1983_11
特許番号
US04416985

反応ノート

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