Sodium borohydride → 11beta-Fluoro-7alpha-{5-[methyl-(9,9,10,10,10-pentafluoro-decyl)-amino]-pentyl}-estra-1,3,5(10)-triene-3,17beta-diol

HRID 1837227Notes

Reaction equation

HRID 1837227 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:43])=[CH:8][C:9]=1[CH2:10][C@H:11]2[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][N:26]([CH3:42])[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][C:35]([F:41])([F:40])[C:36]([F:39])([F:38])[F:37].[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:43])=[CH:8][C:9]=1[CH2:10][C@H:11]2[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][N:26]([CH3:42])[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][C:35]([F:40])([F:41])[C:36]([F:37])([F:38])[F:39]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 1587066611beta-Fluoro-3-hydroxy-7alpha-{5-[methyl-(9,9,10,10,10-pentafluoro-decyl)-amino]-pentyl}-estra-1,3,5(10)-trien-17-one

Product 1

HCID 987384011beta-Fluoro-7alpha-{5-[methyl-(9,9,10,10,10-pentafluoro-decyl)-amino]-pentyl}-estra-1,3,5(10)-triene-3,17beta-diolYield 45.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

92 mg of 11β-fluoro-3-hydroxy-7α-{5-[methyl-(9,9,10,10,10-pentafluoro-decyl)-amino]-pentyl}-estra-1,3,5(10)-trien-17-one is dissolved in 2 ml of methanol and mixed with 23 mg of sodium borohydride. After 1 hour of stirring at room temperature, the solvent is drawn off in a vacuum for the most part, the residue is mixed with common salt solution, extracted 3 times with methylene chloride, dried on magnesium sulfate and concentrated by evaporation in a vacuum. Preparative thin-layer chromatography with methylene chloride/methanol=9/1 as a mobile solvent provides 42 mg of 11β-fluoro-7α-{5-[methyl-(9,9,10,10,10-pentafluoro-decyl)-amino]-pentyl}-estra-1,3,5(10)-triene-3,17β-diol as a foam, [α]D=+44° (c=1.0 in chloroform).

Workup

  1. additionthe residue is mixed with common salt solution
  2. extractionextracted 3 times with methylene chloride
  3. customdried on magnesium sulfate
  4. concentrationconcentrated by evaporation in a vacuum

Sources & evidence

ORD record
ord-80d5eba735df4a678fcb86e472d05b1d
Source dataset
uspto-grants-2004_08
Patent number
US06780855B2

Reaction notes

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