Triphenylstannane → HCID 68147036, compound

HRID 1658713Notes

Reaction equation

HRID 1658713 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])[CH:17]=[CH:18]1)[CH:13]=[CH:12]3)(=[O:3])[CH3:2].C1([SnH](C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>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])[CH:17]=[CH:18]1)[CH:13]=[CH:12]3)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 6460TriphenylstannaneHCID 68146585HCID 68146585, compound

Product 1

HCID 68147036HCID 68147036, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

230 mg. of 17β-acetoxy-9-bromo-11β-fluoro-1,4,6-androstatrien-3-one is stirred at room temperature for 5 hours in 7 ml. of tetrahydrofuran with 1 ml. of triphenyltin hydride while adding 1 mg. of α,α'-azoisobutyrodinitrile. The solution is worked up as disclosed in Example 1. After purification by preparative layer chromatography, 70 mg. of 17β-acetoxy-11β-fluoro-1,4,6-androstatrien-3-one is isolated. UV: ε298 = 11,800 (methanol).

Workup

  1. customAfter purification by preparative layer chromatography, 70 mg

Sources & evidence

ORD record
ord-b38879204825466683b2b05bd096d95c
Source dataset
uspto-grants-1976_06
Patent number
US03966713

Reaction notes

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