Sodium borohydride → HCID 131724565, compound

HRID 1837252Notes

Reaction equation

HRID 1837252 reaction equation
[F:1][C:2]([C:33]([F:48])([F:47])[C:34]([F:46])([F:45])[C:35]([F:44])([F:43])[C:36]([F:42])([F:41])[C:37]([F:40])([F:39])[F:38])=[CH:3][CH2:4][N:5]([CH3:32])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C@@H:11]1[CH2:28][C:27]2[CH:26]=[C:25]([OH:29])[CH:24]=[CH:23][C:22]=2[C@@H:21]2[C@@H:12]1[C@H:13]1[C@@:17]([CH2:19][C@@H:20]2[F:30])([CH3:18])[C:16](=[O:31])[CH2:15][CH2:14]1.[BH4-].[Na+]>CO>[F:1][C:2]([C:33]([F:47])([F:48])[C:34]([F:45])([F:46])[C:35]([F:43])([F:44])[C:36]([F:41])([F:42])[C:37]([F:40])([F:39])[F:38])=[CH:3][CH2:4][N:5]([CH3:32])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C@@H:11]1[CH2:28][C:27]2[CH:26]=[C:25]([OH:29])[CH:24]=[CH:23][C:22]=2[C@@H:21]2[C@@H:12]1[C@H:13]1[C@@:17]([CH2:19][C@@H:20]2[F:30])([CH3:18])[C@@H:16]([OH:31])[CH2:15][CH2:14]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 131724564HCID 131724564, compound

Product 1

HCID 131724565HCID 131724565, compoundYield 13.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2.4 g of 7α-{5-[(3,4,4,5,5,6,6,7,7,8,8,8-dodecafluor-oct-2-enyl)-methyl-amino]-pentyl}-11β-fluoro-3-hydroxy-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 eluant, 319 mg of 7α-{5-[(3,4,4,5,5,6,6,7,7,8,8,8-dodecafluor-oct-2-enyl)-methyl-amino]-pentyl}-11β-fluor-estra-1,3,5(10)-triene-3,17β-diol is obtained as a foam, [α]D=+37° (c=0.5 in CHCl3).

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 eluant

Sources & evidence

ORD record
ord-68c00ec43d8f444f98595013a9a4902a
Source dataset
uspto-grants-2004_08
Patent number
US06780855B2

Reaction notes

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