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Sulfuric Acid → (3beta,5beta,15alpha,16alpha)-15,16-Dihydro-3,5-dihydroxy-3'H-cycloprop(15,16)androsta-6,15-dien-17-one
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Sulfuric Acid | HCID 1118 | — |
| 反応物 | Potassium Hydroxide | HCID 14797 | — |
| 反応物 | Sodium Perchlorate | HCID 522606 | — |
| 反応物 | 5-Hydroxy-15 beta,16 beta-methylene-3 beta-pivaloyloxy-5 beta-androst-6-en-17-one | HCID 13075972 | — |
| 溶媒 | Methanol | HCID 887 | — |
| 溶媒 | Water | HCID 962 | — |
| 溶媒 | Tetrahydrofuran | HCID 8028 | — |
| 生成物 | (3beta,5beta,15alpha,16alpha)-15,16-Dihydro-3,5-dihydroxy-3'H-cycloprop(15,16)androsta-6,15-dien-17-one | HCID 13075974 | 94.3% |
反応手順
134 g of 5-hydroxy-15β,16β-methylene-3β-pivaloyloxy-5β-androst-6-en-17-one is dissolved in 1340 ml of tetrahydrofuran and 670 ml of methanol and combined in succession with 40 g of pulverized potassium hydroxide 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 precipitated solid product is removed by filtration. After dissolving in methylene chloride and drying with sodium sulfate, the product is concentrated under vacuum. By trituration of the resultant solid compound with ethyl acetate, 99.8 g of 3β,5-dihydroxy-15β,16β-methylene-5β-androst-6-en-17-one is obtained, mp 196.5°-198° C.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US04435327 |
| 出典データセット | uspto-grants-1984_03 |
| ORD ID | ord-176988101f7c417e857e3bb56d9f2b4a |
| 出典メモ | uspto-grants-1984_03 |