Tributylstannane → HCID 68147202, compound

HRID 1658704Notes

Reaction equation

HRID 1658704 reaction equation
[C:1]([O:4][C@H:5]1[CH2:10][CH2:9][C@H:8]2[C@H:11]3[C@:21](Br)([C@@H:22]([F:24])[CH2:23][C@:6]12[CH3:7])[C@:19]1([CH3:20])[C:14](=[CH:15][C:16](=[O:26])[CH2:17][CH2:18]1)[CH2:13][CH2:12]3)(=[O:3])[CH3:2].C([SnH](CCCC)CCCC)CCC>O1CCCC1>[C:1]([O:4][C@H:5]1[CH2:10][CH2:9][C@H:8]2[C@H:11]3[C@H:21]([C@@H:22]([F:24])[CH2:23][C@:6]12[CH3:7])[C@:19]1([CH3:20])[C:14](=[CH:15][C:16](=[O:26])[CH2:17][CH2:18]1)[CH2:13][CH2:12]3)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 5948TributylstannaneHCID 68146927HCID 68146927, compound

Product 1

HCID 68147202HCID 68147202, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

8 g. of 17β-acetoxy-9-bromo-11β-fluoro-4-androsten-3-one is agitated at room temperature for 5 hours in 160 ml. of tetrahydrofuran with 20 ml. of tributyltin hydride with the addition of 10 mg. of α ,α'-azoisobutyrodinitrile. The solution is evaporated under vacuum; the residue is crystallized with hexane. The crystalline product is vacuum-filtered and chromatographed on silica gel for further purification. With ethyl acetate/hexane, 3.4 g. of 17β-acetoxy-11β-fluoro-4-androsten-3-one is obtained as the elution product; m.p. 165°-167° (decomposition). UV: ε239 = 16,400 (methanol).

Workup

  1. customThe solution is evaporated under vacuum
  2. customthe residue is crystallized with hexane
  3. filtrationThe crystalline product is vacuum-filtered
  4. customchromatographed on silica gel for further purification

Sources & evidence

ORD record
ord-31931f1ab0a74aa1b65fb33d2f7291a4
Source dataset
uspto-grants-1976_06
Patent number
US03966713

Reaction notes

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