17-Iodoandrosta-5,16-dien-3beta-ol Chemical Properties

Melting point:

175-176℃

Boiling point:

447.5±45.0 °C(Predicted)

Density 

1.45

storage temp. 

2-8°C(protect from light)

solubility 

Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)

pka

14.69±0.70(Predicted)

form 

Solid

color 

White to Off-White

InChI

InChI=1/C19H27IO/c1-18-9-7-13(21)11-12(18)3-4-14-15-5-6-17(20)19(15,2)10-8-16(14)18/h3,6,13-16,21H,4-5,7-11H2,1-2H3/t13-,14-,15-,16-,18-,19-/s3

InChIKey

DHZJEYGWSNDRGN-XEZBUBAUNA-N

SMILES

[C@@H]1(O)CC2[C@](C)(CC1)[C@]1([H])[C@]([H])([C@@]3([H])[C@@](CC1)(C)C(I)=CC3)CC=2 |&1:0,4,8,10,12,14,r|

17-Iodoandrosta-5,16-dien-3beta-ol Usage And Synthesis

Uses

17-Iodoandrosta-5,16-dien-3β-ol is used in synthesis of Oxoabiraterone Acetate.Also, in preparation of Abiraterone Acetate.

Synthesis

As an example, the synthesis of 17-iodo-androsta-5,16-dien-3β-ol (13) was carried out: iodine (12.16 g, 0.0203 mol) was dissolved in anhydrous THF (144 mL) and dry Et2O (72 mL), stirred and cooled to 0 °C in an ice bath. Subsequently, 1,1,3,3-tetramethylguanidine (6.72 mL, 6.24 g, 0.054 mol) was added to this solution. A THF (81 mL) solution of compound 12 (3.0 g, 9.9 mmol) was slowly added dropwise to the above iodine solution over a period of 2 hrs, ensuring that the reaction temperature was maintained at 0°C. Upon completion of the reaction, the mixture was concentrated under vacuum, cooled to ice bath temperature and then dried under vacuum at room temperature to give the yellow solid product 13 (3.65 g, 92.4% yield). The melting point of the product was 169-171 °C (literature value 175-176 °C); IR (CHCl3) showed absorption peaks located at 2935, 1371, 1039, 862, 843, 799, 715, 665, 582 and 566 cm-1 ; 1H NMR (300 MHz, CDCl3) δ value: 0.76 (s, 3H, 18-CH3), and 1.05 (s, 3H, 19-CH3), 3.50 (br s, 1H, 3α-H), 5.35 (s, 1H, 6-H) and 6.14 (s, 1H, 16-H).

References

[1] Tetrahedron Letters, 1983, vol. 24, # 15, p. 1605 - 1608
[2] Journal of Medicinal Chemistry, 2005, vol. 48, # 8, p. 2972 - 2984
[3] Patent: WO2006/93993, 2006, A1. Location in patent: Page/Page column 31; 45
[4] Patent: CN102627681, 2016, B. Location in patent: Paragraph 0028; 0029
[5] Patent: WO2013/30410, 2013, A2. Location in patent: Page/Page column 28-29

17-Iodoandrosta-5,16-dien-3beta-ol(32138-69-5)Related Product Information

• Stearic acid
• 1-Indanone
• Tenofovir
• Benzoyl chloride
• 4-Dimethylaminopyridine
• Imatinib
• ETHYLENE OXIDE
• Boric acid
• Androstenone hydrazone
• ABiraterone impurity 15
• Abiraterone Acetate Dimer Impurity
• (3β)-Androsta-5,16-diene-3,17-diol 3-Acetate 17-(Trifluoromethanesulfonate)
• DIETHYL(3-PYRIDYL)BORANE
• Abiraterone Sulfate Sodium Salt
• Abiraterone Impurity 4
• Abiraterone Ethyl Ether
• Dehydroepiandrosterone acetate
• Abiraterone