Sodium borohydride → HCID 15858642, compound

HRID 1837234Notes

Reaction equation

HRID 1837234 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:28])=[CH:8][C:9]=1[CH2:10][C@H:11]2[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][NH:26][CH3:27].[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:28])=[CH:8][C:9]=1[CH2:10][C@H:11]2[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][NH:26][CH3:27]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 1587066511beta-Fluoro-3-hydroxy-7alpha-[5-(methylamino)-pentyl]-estra-1,3,5(10)-trien-17-one

Product 1

HCID 15858642HCID 15858642, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

880 mg of 11β-fluoro-3-hydroxy-7α-(5-(methyl-amino)-pentyl)-estra-1,3,5(10)-trien-17-one is dissolved in 15 ml of methanol, mixed in portions with 252 mg of sodium borohydride and stirred for 15 minutes at room temperature. For working-up, the reaction solution is added to saturated common salt solution, extracted several times with methylene chloride, the organic phases are washed with water, dried on magnesium sulfate and concentrated by evaporation in a vacuum. 540 mg of 11β-fluoro-7α-(5-(methyl-amino)-pentyl)-estra-1,3,5(10)-triene-3,17β-diol is obtained as a foam, [α]D=+63° (c=0.5 in chloroform).

Workup

  1. additionthe reaction solution is added to saturated common salt solution
  2. extractionextracted several times with methylene chloride
  3. washthe organic phases are washed with water
  4. customdried on magnesium sulfate
  5. concentrationconcentrated by evaporation in a vacuum

Sources & evidence

ORD record
ord-d165227c4f6f4cc6a005d655891f9466
Source dataset
uspto-grants-2004_08
Patent number
US06780855B2

Reaction notes

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