Ethanol → 7alpha-(5-Bromopentyl)-11beta-fluorooestra-1,3,5(10)-triene-3,17beta-diol

HRID 650369ノート

反応式

HRID 650369 の反応式
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C@@H:7]1[CH2:24][C:23]2[CH:22]=[C:21]([OH:25])[CH:20]=[CH:19][C:18]=2[C@@H:17]2[C@@H:8]1[C@H:9]1[C@@:13]([CH2:15][C@@H:16]2[F:26])([CH3:14])[C:12](=[O:27])[CH2:11][CH2:10]1.C(O)C.O.[BH4-].[Na+]>O1CCCC1.CCCCCC.C(OCC)(=O)C>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C@@H:7]1[CH2:24][C:23]2[CH:22]=[C:21]([OH:25])[CH:20]=[CH:19][C:18]=2[C@@H:17]2[C@@H:8]1[C@H:9]1[C@@:13]([CH2:15][C@@H:16]2[F:26])([CH3:14])[C@@H:12]([OH:27])[CH2:11][CH2:10]1

参加物

7

反応物 4

HCID 702EthanolHCID 962Water2 回HCID 4311764Sodium borohydrideHCID 1587066311beta-Fluoro-7alpha-(5-bromopentyl)-3-hydroxy-estra-1,3,5(10)-trien-17-one

生成物 1

HCID 158706647alpha-(5-Bromopentyl)-11beta-fluorooestra-1,3,5(10)-triene-3,17beta-diol収率 95.9%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 21226206Ethyl acetate hexane溶媒

反応条件

温度
0 °C

実験手順

A solution of 16.2 g of 7α-(5-bromopentyl)-11β-fluoro-3-hydroxy-estra-1,3,5(10)-trien-17-one in 162 ml of tetrahydrofuran as well as 90 ml of ethanol and 36 ml of water are mixed in portions at 0° C. with 4.7 g of sodium borohydride and stirred for 2 hours at 0° C. Then, it is added to water, extracted four times with ethyl acetate, washed with water and common salt solution, dried on sodium sulfate and concentrated by evaporation in a vacuum. 17.1 g of crude product is obtained. After chromatography on silica gel with hexane/ethyl acetate, 15.6 g of pure 7α-(5-bromopentyl)-11β-fluoro-estra-1,3,5(10)-triene-3,17β-diol is obtained.

後処理

  1. extractionextracted four times with ethyl acetate
  2. washwashed with water and common salt solution
  3. customdried on sodium sulfate
  4. concentrationconcentrated by evaporation in a vacuum
  5. custom17.1 g of crude product is obtained

出典と根拠

ORDレコード
ord-6913aae94ed0469d94db88e4158af244
出典データセット
uspto-grants-2001_08
特許番号
US06271403B1

反応ノート

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