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 1837238Notes

Reaction equation

HRID 1837238 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: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]

Participants

4

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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).

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 a methylene chloride-methanol gradient

Sources & evidence

ORD record
ord-c849f67cbe9b4f0c98288c352019e11a
Source dataset
uspto-grants-2004_08
Patent number
US06780855B2

Reaction notes

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