Sodium Chloride → 11beta-Fluoro-7alpha-{5-[(3,4,4,5,5,5-hexafluoropent-2-enyl)methyl-amino]pentyl}oestra-1,3,5(10)-triene-3,17beta-diol

HRID 1838915ノート

反応式

HRID 1838915 の反応式
[F:1][C@H:2]1[CH2:19][C@@:17]2([CH3:18])[C@@H:13]([CH2:14][CH2:15][C:16]2=[O:20])[C@H:12]2[C@H:3]1[C:4]1[CH:5]=[CH:6][C:7]([OH:39])=[CH:8][C:9]=1[CH2:10][C@H:11]2[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][N:26]([CH2:28][CH:29]=[C:30]([F:38])[C:31]([F:37])([F:36])[C:32]([F:35])([F:34])[F:33])[CH3:27].[BH4-].[Na+].[Cl-].[Na+]>CO>[F:1][C@H:2]1[CH2:19][C@@:17]2([CH3:18])[C@@H:13]([CH2:14][CH2:15][C@@H:16]2[OH:20])[C@H:12]2[C@H:3]1[C:4]1[CH:5]=[CH:6][C:7]([OH:39])=[CH:8][C:9]=1[CH2:10][C@H:11]2[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][N:26]([CH2:28][CH:29]=[C:30]([F:38])[C:31]([F:36])([F:37])[C:32]([F:33])([F:34])[F:35])[CH3:27]

参加物

5

反応物 3

HCID 5234Sodium ChlorideHCID 4311764Sodium borohydrideHCID 86587645HCID 86587645、化合物

生成物 1

HCID 8658764611beta-Fluoro-7alpha-{5-[(3,4,4,5,5,5-hexafluoropent-2-enyl)methyl-amino]pentyl}oestra-1,3,5(10)-triene-3,17beta-diol収率 12.9%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

1.86 g of 11β-fluoro-7α-{5-[(3,4,4,5,5,5-hexafluoro-pent-2-enyl)methylamino]pentyl}-3-hydroxyestra-1,3,5(10)-trien-17-one are dissolved in 15 ml of methanol and cautiously treated with 222 mg of sodium borohydride. After stirring at room temperature for 15 minutes, the mixture is added to saturated sodium chloride solution, extracted with methylene chloride, dried over magnesium sulphate and concentrated in vacuo. After chromatographing the crude product on silica gel using a hexane-ethyl acetate and an ethyl acetate-acetone gradient, 241 mg of 11β-fluoro-7α-{5-[(3,4,4,5,5,5-hexafluoropent-2-enyl)methyl-amino]pentyl}oestra-1,3,5(10)-triene-3,17β-diol of melting point 122° C. are obtained, [α]D=+47° (c=0.5 in CHCl3)

後処理

  1. extractionextracted with methylene chloride
  2. dry with materialdried over magnesium sulphate
  3. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-7f559eab67d34012afa3fd7db6a9fc17
出典データセット
uspto-grants-2004_01
特許番号
US06677324B1

反応ノート

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