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

HRID 65416

반응식

HRID 65416 반응식
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

참가 물질

5

반응물 2

HCID 8028TetrahydrofuranHCID 130759667alpha-Chloro-5,6beta-epoxy-3beta-hydroxy-15beta,16beta-methylene-5beta-androstan-17-one

생성물 1

HCID 13075974(3beta,5beta,15alpha,16alpha)-15,16-Dihydro-3,5-dihydroxy-3'H-cycloprop(15,16)androsta-6,15-dien-17-one수율 94.4%

시약·촉매·용매 2

HCID 23994Zinc촉매HCID 176Acetic Acid용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-4f6f033bf183440a905cf0a17ebf7a0c
출처 데이터셋
uspto-grants-1986_09
특허 번호
US04614616

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