N-Boc-4-iodopiperidine synthesis
- Product Name:N-Boc-4-iodopiperidine
- CAS Number:301673-14-3
- Molecular formula:C10H18INO2
- Molecular Weight:311.16
109384-19-2
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301673-14-3
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Yield:301673-14-3 93%
Reaction Conditions:
with 1H-imidazole;iodine;triphenylphosphine in dichloromethane at 0 - 20; for 18 h;
Steps:
24.A Part A. Preparation of iodo Intermediate
To a solution of N-Boc-4-hydroxypiperdine (10.0 g, 49.7 mmol) in dichloromethane (200 mL) was added triphenylphosphine (16.9 g, 64.6 mmol) and imidazole (5.07 g, 74.5 mmol). The resulting slurry was cooled to 0° C. in an ice bath. Iodine (15.1 g, 59.6 mmol) was added in small portions. The solution was then stirred for 18 hr at ambient temperature. Afterward, the solution was diluted with water and extracted with diethyl ether. The organic layer was washed with water and saturated aqueous NaCl, and then dried over sodium sulfate. Concentration in vacuo followed by trituration with hexane removed the excess triphenylphosphine and triphenylphosphine oxide. The filtrate was concentrated in vacuo to provide the iodo intermediate as a colorless oil (14.4 g, 93% yield).
References:
Barta, Thomas E.;Becker, Daniel P.;Bedell, Louis J.;Boehm, Terri L.;Brown, David L.;Carroll, Jeffery N.;Chen, Yiyuan;Fobian, Yvette M.;Freskos, John N.;Gasiecki, Alan F.;Grapperhaus, Margaret L.;Heintz, Robert M.;Hockerman, Susan L.;Kassab, Darren J.;Khanna, Ish K.;Kolodziej, Stephen A.;Massa, Mark A.;McDonald, Joseph J.;Mischke, Brent V.;Mischke, Deborah A.;Mullins, Patrick B.;Nagy, Mark A.;Norton, Monica B.;Rico, Joseph G.;Schmidt, Michelle A.;Stehle, Nathan W.;Talley, John J.;Vernier, William F.;Villamil, Clara I.;Wang, Lijuan J.;Wynn, Thomas A. US2005/9838, 2005, A1 Location in patent:Page 143
288-32-4
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109384-19-2
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301673-14-3
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84358-13-4
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301673-14-3
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5382-16-1
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301673-14-3
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24424-99-5
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301673-14-3
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