17-Iodoandrosta-5,16-dien-3beta-ol synthesis
- Product Name:17-Iodoandrosta-5,16-dien-3beta-ol
- CAS Number:32138-69-5
- Molecular formula:C19H27IO
- Molecular Weight:398.32
63015-10-1
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Yield:32138-69-5 92.4%
Reaction Conditions:
with iodine;N,N,N',N'-tetramethylguanidine in tetrahydrofuran;diethyl ether at 0; for 2 h;
Steps:
17-Iodoandrosta-5,16-diene-3β-ol (13): A stirred solution of iodine (12.16 g, .0203 mol) in dry of THF (144 mL) and dry OfEt2O (72 mL) was cooled in an ice bath to 0 0C and the solution was treated with 1,1,3,3, tetramethylguanidine (6.72 mL, 6.24g, .054 mole). A solution of compound 12 (3.0 g, 9.9 mmol) in THF (81 mL) was added dropwise to the iodine solution over 2 h maintaining the reaction temperature at 0 0C. The reaction mixture was then concentrated under vacuum, cooled in an ice-bath, and then dried to under vacuum at roomtemperature to afford a yellow solid (13, 3.65 g, 92.4%). mp: 169-171 0C. (lit. 175-176 0C);22 IR (CHCl3) 2935, 1371, 1039, 862, 843, 799, 715, 665, 582, and 566 cm"1; 1HNMR (300MHz, CDCl3): δ 0.76 (s, 3H, 18-CH3), 1.05 (s, 3H, 19-CH3), 3.50 (br s, IH, 3α-H), 5.35 (s,IH, 6-H) and 6.14 (s, IH, 16-H).
References:
WO2006/93993,2006,A1 Location in patent:Page/Page column 31; 45
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