Iodine → 17beta-Acetoxy-2-iodo-1alpha-methyl-androst-4-en-3-one

HRID 275070Notes

Reaction equation

[C:1]([O:4][C@H:5]1[CH2:10][CH2:9][C@H:8]2[C@H:11]3[C@H:21]([CH2:22][CH2:23][C@:6]12[CH3:7])[C@:19]1([CH3:20])[C:14](=[CH:15][C:16](=[O:25])[CH2:17][C@@H:18]1[CH3:24])[CH2:13][CH2:12]3)(=[O:3])[CH3:2].[I:26]I>C(O)(=O)C>[C:1]([O:4][C@H:5]1[CH2:10][CH2:9][C@H:8]2[C@H:11]3[C@H:21]([CH2:22][CH2:23][C@:6]12[CH3:7])[C@:19]1([CH3:20])[C:14](=[CH:15][C:16](=[O:25])[CH:17]([I:26])[C@@H:18]1[CH3:24])[CH2:13][CH2:12]3)(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 60 °C

Procedure

6.88 g (20 mmol) of 17β-acetoxy-1α-methyl-androst-4-en-3-one and 1.75 g (22 mmol) of CuO in 60 ml of acetic acid are mixed with stirring at room temperature with 5.58 g (22 mmol) of iodine and stirred under nitrogen atmosphere for 24 hours at 60° C. Under reduced pressure, the acetic acid is largely distilled off and the residue is taken up in 100 ml of water. The water phase is extracted 3 times with 100 ml of ethyl acetate each. The ethyl acetate phases are washed with sodium thiosulfate solution and dried on sodium sulfate. After concentration by evaporation of the solution, 10 g of crude product is obtained. Recrystallization from ethyl acetate yields 8.8 g of 17β-acetoxy-2-iodo-1α-methyl-androst-4-en-3-one (93% of theory) of melting point 102° C.

Workup

distillationUnder reduced pressure, the acetic acid is largely distilled off
extractionThe water phase is extracted 3 times with 100 ml of ethyl acetate each
washThe ethyl acetate phases are washed with sodium thiosulfate solution
customdried on sodium sulfate
concentrationAfter concentration
customby evaporation of the solution
custom10 g of crude product is obtained
customRecrystallization from ethyl acetate

Sources & evidence

ORD record: ord-4888f098901b4f7f97854089f232c0f4
Source dataset: uspto-grants-1995_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05391778

Reaction notes

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