Triphenylstannane → HCID 13990933, compound

HRID 1658712Notes

Reaction equation

HRID 1658712 reaction equation
Cl[C@:2]12[C@@H:19]([F:20])[CH2:18][C@@:16]3([CH3:17])[C@@H:12]([CH2:13][CH2:14][C:15]3=[O:21])[C@@H:11]1[CH2:10][CH2:9][C:8]1[C@:3]2([CH3:23])[CH2:4][CH2:5][C:6](=[O:22])[CH:7]=1.C1([SnH](C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[F:20][C@H:19]1[CH2:18][C@@:16]2([CH3:17])[C@@H:12]([CH2:13][CH2:14][C:15]2=[O:21])[C@H:11]2[C@H:2]1[C@:3]1([CH3:23])[C:8]([CH2:9][CH2:10]2)=[CH:7][C:6](=[O:22])[CH2:5][CH2:4]1

Participants

4

Reactant 2

HCID 6460TriphenylstannaneHCID 68147319HCID 68147319, compound

Product 1

HCID 13990933HCID 13990933, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.2 g. of 9-chloro-11β-fluoro-4-androstene-3,17-dione is agitated for 2 hours at room temperature in 20 ml. of tetrahydrofuran and 3 ml. of triphenyltin hydride with the addition of 7 mg. of α,α'-azoisobutyrodinitrile. The solution is evaporated under vacuum and worked up as set forth in Example 1. After purification by preparative layer chromatography, 380 mg. of 11β-fluoro-4-androstene-3,17-dione is obtained; m.p. 162°-164°. UV: ε238 = 16,300 (methanol).

Workup

  1. customThe solution is evaporated under vacuum
  2. customAfter purification by preparative layer chromatography, 380 mg

Sources & evidence

ORD record
ord-af5328098c15477cb55bb1db52bda48a
Source dataset
uspto-grants-1976_06
Patent number
US03966713

Reaction notes

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