Sodium borohydride → 11beta-Fluoro-7alpha-{5-[methyl-(3,4,4,5,5,6,6,6-octafluoro-hex-2-enyl)-amino]-pentyl}-estra-1,3,5(10)-triene-3,17beta-diol

HRID 1837250Notes

Reaction equation

HRID 1837250 reaction equation
[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:42])=[CH:8][C:9]=1[CH2:10][C@H:11]2[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][N:26]([CH3:41])[CH2:27][CH:28]=[C:29]([F:40])[C:30]([F:39])([F:38])[C:31]([F:37])([F:36])[C:32]([F:35])([F:34])[F:33].[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:42])=[CH:8][C:9]=1[CH2:10][C@H:11]2[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][N:26]([CH3:41])[CH2:27][CH:28]=[C:29]([F:40])[C:30]([F:38])([F:39])[C:31]([F:36])([F:37])[C:32]([F:33])([F:34])[F:35]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86587647HCID 86587647, compound

Product 1

HCID 8658764811beta-Fluoro-7alpha-{5-[methyl-(3,4,4,5,5,6,6,6-octafluoro-hex-2-enyl)-amino]-pentyl}-estra-1,3,5(10)-triene-3,17beta-diolYield 4.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1.7 g of 11β-fluoro-3-hydroxy-7α-{5-[methyl-(3,4,4,5,5,6,6,6-octafluoro-hex-2-enyl)-amino]-pentyl}-estra-1,3,5(10)-trien-17-one is dissolved in 15 ml of methanol and carefully mixed with 222 mg of sodium borohydride. After 15 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 ethyl acetate as an eluent, 84 mg of 11β-fluoro-7α-{5-[methyl-(3,4,4,5,5,6,6,6-octafluoro-hex-2-enyl)-amino]-pentyl}-estra-1,3,5(10)-triene-3,17β-diol with a melting point of 130° C. is obtained.

Workup

  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 ethyl acetate as an eluent

Sources & evidence

ORD record
ord-f1876dc2e0964852b325d0fe593dc538
Source dataset
uspto-grants-2004_08
Patent number
US06780855B2

Reaction notes

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