Sodium borohydride → 11beta-Fluoro-7alpha-(5-pyrrolidin-1-yl-pentyl)-estra-1,3,5(10)-triene-3,17beta-diol

HRID 1837236Notes

Reaction equation

HRID 1837236 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:31])=[CH:8][C:9]=1[CH2:10][C@H:11]2[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][N:26]1[CH2:30][CH2:29][CH2:28][CH2:27]1.[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:31])=[CH:8][C:9]=1[CH2:10][C@H:11]2[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][N:26]1[CH2:27][CH2:28][CH2:29][CH2:30]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 69916435HCID 69916435, compound

Product 1

HCID 1585864811beta-Fluoro-7alpha-(5-pyrrolidin-1-yl-pentyl)-estra-1,3,5(10)-triene-3,17beta-diol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

324 mg of 11β-fluoro-3-hydroxy-7α-(5-pyrrolidin-1-yl-pentyl)-estra-1,3,5(10)-trien-17-one is dissolved in 10 ml of methanol and mixed with 63 mg of sodium borohydride. After 1.5 hours of stirring at room temperature, the batch is added to semi-saturated common salt solution, extracted 3 times 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, 192 mg of 11β-fluoro-7α-(5-pyrrolidin-1-yl)-pentyl)-estra-1,3,5(10)-triene-3,17β-diol with a melting point of 95-118° C. is obtained.

Workup

  1. additionthe batch is added to semi-saturated common salt solution
  2. extractionextracted 3 times 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, 192 mg of 11β-fluoro-7α-(5-pyrrolidin-1-yl)-pentyl)-estra-1,3,5(10)-triene-3,17β-diol with a melting point of 95-118° C.
  6. customis obtained

Sources & evidence

ORD record
ord-bbf646c9ea7b456082a1e53dcc50dee5
Source dataset
uspto-grants-2004_08
Patent number
US06780855B2

Reaction notes

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