1-Iodohexane → HCID 15838316, compound

HRID 1938916Notes

Reaction equation

HRID 1938916 reaction equation
[OH:1][C@H:2]1[CH2:7][CH2:6][C@H:5]2[C@H:8]3[C@H:18]([CH2:19][CH2:20][C@:3]12[CH3:4])[C@:16]1([CH3:17])[C@H:11]([N:12]([CH3:22])[C:13](=[O:21])[CH2:14][CH2:15]1)[CH2:10][CH2:9]3.[OH-].[K+].[CH2:25](I)[CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]>CS(C)=O.O>[CH2:25]([O:1][C@H:2]1[CH2:7][CH2:6][C@H:5]2[C@H:8]3[C@H:18]([CH2:19][CH2:20][C@:3]12[CH3:4])[C@:16]1([CH3:17])[C@H:11]([N:12]([CH3:22])[C:13](=[O:21])[CH2:14][CH2:15]1)[CH2:10][CH2:9]3)[CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]

Participants

6

Reactant 3

HCID 125271-IodohexaneHCID 14797Potassium HydroxideHCID 10171822HCID 10171822, compound

Product 1

HCID 15838316HCID 15838316, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a solution of 17β-hydroxy-4-methyl-5α-4-azaandrostan-3-one (102 mg, 0.336 mmol) in DMSO (3 ml) was added powdered KOH (300 mg) followed by n-hexyliodide (400 μl). After stirring the reaction mixture overnight, the reaction was diluted with water and extracted with ethyl acetate. The organic layer was washed with water, then brine, then dried (MgSO4), and concentrated in vacuo. The residue was then purified by preparative thin layer chromatography to afford the title compound, characterized by H1NMR.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialbrine, then dried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe residue was then purified by preparative thin layer chromatography

Sources & evidence

ORD record
ord-1751fb7c7ddd49c6abfb2d0db9b0ec09
Source dataset
uspto-grants-1997_12
Patent number
US05693809

Reaction notes

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