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

HRID 65416

反応式

HRID 65416 の反応式
Cl[C@@H:2]1[C@H:19]2[O:20][C@:18]32[C@:13]([CH3:22])([CH2:14][CH2:15][C@H:16]([OH:21])[CH2:17]3)[C@@H:12]2[C@@H:3]1[C@H:4]1[C@@:8]([CH2:10][CH2:11]2)([CH3:9])[C:7](=[O:23])[C@H:6]2[CH2:24][C@@H:5]12.O1CCCC1>C(O)(=O)C.[Zn]>[OH:21][C@H:16]1[CH2:15][CH2:14][C@@:13]2([CH3:22])[C@:18]([OH:20])([CH:19]=[CH:2][C@@H:3]3[C@@H:12]2[CH2:11][CH2:10][C@@:8]2([CH3:9])[C@H:4]3[C@@H:5]3[CH2:24][C@@H:6]3[C:7]2=[O:23])[CH2:17]1

参加物

5

反応物 2

HCID 8028TetrahydrofuranHCID 130759667alpha-Chloro-5,6beta-epoxy-3beta-hydroxy-15beta,16beta-methylene-5beta-androstan-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 94.4%

試薬・触媒・溶媒 2

HCID 23994Zinc触媒HCID 176Acetic Acid溶媒

実験手順

107.5 g of 7α-chloro-5,6β-epoxy-3β-hydroxy-15β,16β-methylene-5β-androstan-17-one is dissolved in 500 ml of acetic acid and 500 ml of tetrahydrofuran and, after the addition of 324 g of zinc dust in three portions, stirred at room temperature for 16 hours. The zinc is then filtered off, the filtrate is diluted with methylene chloride, and washed with sodium bicarbonate solution and water. After drying over sodium sulfate, the product is concentrated under vacuum. By trituration of the thus-obtained solid with ethyl acetate, 91.5 g of 3β,5-dihydroxy-15β,16β-methylene-5β-androst-6-en-17-one is produced, mp 196° C.

後処理

  1. filtrationThe zinc is then filtered off
  2. additionthe filtrate is diluted with methylene chloride
  3. washwashed with sodium bicarbonate solution and water
  4. dry with materialAfter drying over sodium sulfate
  5. concentrationthe product is concentrated under vacuum

出典と根拠

ORDレコード
ord-4f6f033bf183440a905cf0a17ebf7a0c
出典データセット
uspto-grants-1986_09
特許番号
US04614616

関連ノート

読み込み中…