関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | Imidazole | HCID 795 | — |
| 反応物 | Iodine | HCID 807 | — |
| 反応物 | Triphenylphosphine | HCID 11776 | — |
| 反応物 | Sodium Thiosulfate | HCID 24477 | — |
| 反応物 | 1-(tert-Butoxycarbonyl)-4-(2-hydroxyethyl)piperidine | HCID 854140 | — |
| 触媒 | Copper Sulfate | HCID 24462 | — |
| 溶媒 | Diethyl Ether | HCID 3283 | — |
| 溶媒 | Acetonitrile | HCID 6342 | — |
| 溶媒 | Sodium chloride; water | HCID 57417360 | — |
| 生成物 | Tert-butyl 4-(2-iodoethyl)piperidine-1-carboxylate | HCID 9974426 | — |
反応手順
Combined 4-(2-hydroxyeth-1-yl)-1-tert-butoxylcarbonylpiperidine (37.4 g, 0.16 mol, from Step B), triphenylphosphine (55 g, 0.21 mol) and imidazole (14 g, 0.21 mol) in 800 mL of 33% acetonitrile in ether. Cooled to 0° C. and added iodine (56 g, 0.22 mol) portionwise. The iodine is de-colored until the endpoint of the reaction. Diluted with 1 L of ether. Washed organic layer with 2×500 mL each of sat'd. aq. Na2S2O3, sat. aq. CuSO4 and brine. Dried over magnesium sulfate, filtered and concentrated. Triphenylphosphine oxide precipitates. Added ether and filtered the slurry through a plug of silica gel. Purified a portion of the crude material by flash chromatography (5% ethyl acetate in hexane eluent) to afford the title compound.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 特許番号 | US06358979B1 |
|---|
| 出典データセット | uspto-grants-2002_03 |
|---|
| ORD ID | ord-c83c962e4a924518a69d95c326d2625c |
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| 出典メモ | uspto-grants-2002_03 |
|---|
