Tributylstannane → HCID 69528777, compound

HRID 2215939Notes

Reaction equation

HRID 2215939 reaction equation
Br[C@@H:2]1[C@@H:7]([OH:8])[CH2:6][C@H:5]2[C@@H:9]3[C@H:18]([CH2:19][CH2:20][C@:3]12[CH3:4])[C:17]1[CH:16]=[CH:15][C:14]([O:21][CH3:22])=[CH:13][C:12]=1[CH2:11][CH2:10]3.C([SnH](CCCC)CCCC)CCC.N(C(C)(C)C#N)=NC(C)(C)C#N>O1CCCC1>[CH3:22][O:21][C:14]1[CH:15]=[CH:16][C:17]2[C@@H:18]3[C@@H:9]([C@H:5]4[C@@:3]([CH2:20][CH2:19]3)([CH3:4])[CH2:2][C@@H:7]([OH:8])[CH2:6]4)[CH2:10][CH2:11][C:12]=2[CH:13]=1

Participants

5

Reactant 3

HCID 5948TributylstannaneHCID 6547AzobisisobutyronitrileHCID 15491112HCID 15491112, compound

Product 1

HCID 69528777HCID 69528777, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3.50 g (9.60 mmol) of 17α-bromo-3-methoxy-8α-estra-1,3,5(10)-trien-16β-ol, 3.50 g (12.03 mmol) of tributyl tin hydride and 50 mg of azobisisobutyronitrile in 30 ml of dry tetrahydrofuran is refluxed for 2 hours while being stirred in an argon atmosphere. For working-up, it is allowed to cool, concentrated by evaporation in a vacuum in a Rotavapor, and the residue is taken up in ethyl acetate (300 ml). After the organic phase is washed with aqueous hydrochloric acid, water and brine, it is dried on sodium sulfate. The residue is chromatographed on silica gel (dichloromethane/ethyl acetate, 9:1), yield 2.70 g (98%).

Workup

  1. temperatureto cool
  2. concentrationconcentrated by evaporation in a vacuum in a Rotavapor
  3. washAfter the organic phase is washed with aqueous hydrochloric acid, water and brine, it
  4. customis dried on sodium sulfate
  5. customThe residue is chromatographed on silica gel (dichloromethane/ethyl acetate, 9:1), yield 2.70 g (98%)

Sources & evidence

ORD record
ord-6c78f3c4dad74655853306e346bee6a1
Source dataset
uspto-grants-2006_09
Patent number
US07109360B1

Reaction notes

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