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 1838915노트

반응식

HRID 1838915 반응식
[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]

참가 물질

5

반응물 3

HCID 5234Sodium ChlorideHCID 4311764Sodium borohydrideHCID 86587645HCID 86587645, 화합물

생성물 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-diol수율 12.9%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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)

후처리

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

출처 및 근거

ORD 기록
ord-7f559eab67d34012afa3fd7db6a9fc17
출처 데이터셋
uspto-grants-2004_01
특허 번호
US06677324B1

반응 노트

불러오는 중…