Sodium borohydride → 11beta-Fluoro-7alpha-{5-[methyl-(4,4,5,5,5-pentafluoro-pentyl)-amino]-pentyl}-estra-1,3,5(10)-triene-3,17beta-diol

HRID 1837238노트

반응식

HRID 1837238 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:38])=[CH:8][C:9]=1[CH2:10][C@H:11]2[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][N:26]([CH3:37])[CH2:27][CH2:28][CH2:29][C:30]([F:36])([F:35])[C:31]([F:34])([F:33])[F:32].[BH4-].[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:38])=[CH:8][C:9]=1[CH2:10][C@H:11]2[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][N:26]([CH3:37])[CH2:27][CH2:28][CH2:29][C:30]([F:35])([F:36])[C:31]([F:32])([F:33])[F:34]

참가 물질

4

반응물 2

HCID 4311764Sodium borohydrideHCID 1587066911beta-Fluoro-3-hydroxy-7alpha-{5-[methyl-(4,4,5,5,5-pentafluoro-pentyl)-amino]-pentyl}-estra-1,3,5(10)-trien-17-one

생성물 1

HCID 1585864911beta-Fluoro-7alpha-{5-[methyl-(4,4,5,5,5-pentafluoro-pentyl)-amino]-pentyl}-estra-1,3,5(10)-triene-3,17beta-diol수율 83.1%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

380 mg of 11β-fluoro-3-hydroxy-7α-{5-[methyl-(4,4,5,5,5-pentafluoro-pentyl)-amino]-pentyl}-estra-1,3,5(10)-trien-17-one is dissolved in 25 ml of methanol and mixed with 77 mg of sodium borohydride. After 30 minutes of stirring at room temperature, the batch is added to saturated common salt solution, extracted with methylene chloride, dried on magnesium sulfate and concentrated by evaporation in a vacuum. After the crude product is chromatographed on silica gel with a methylene chloride-methanol gradient, 317 mg of 11β-fluoro-7α-{5-[methyl-(4,4,5,5,5-pentafluoro-pentyl)-amino]-pentyl}-estra-1,3,5(10)-triene-3,17β-diol is obtained as a foam, [α]D=+49° (c=0.5 in methanol).

후처리

  1. additionthe batch is added to saturated common salt solution
  2. extractionextracted with methylene chloride
  3. customdried on magnesium sulfate
  4. concentrationconcentrated by evaporation in a vacuum
  5. customAfter the crude product is chromatographed on silica gel with a methylene chloride-methanol gradient

출처 및 근거

ORD 기록
ord-c849f67cbe9b4f0c98288c352019e11a
출처 데이터셋
uspto-grants-2004_08
특허 번호
US06780855B2

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