참여 물질
| 역할 | 이름 | HCID | 투입량 |
|---|
| 반응물 | Imidazole | HCID 795 | — |
| 반응물 | Iodine | HCID 807 | — |
| 반응물 | Triphenylphosphine | HCID 11776 | — |
| 반응물 | Sodium Thiosulfate | HCID 24477 | — |
| 반응물 | 1-(tert-Butoxycarbonyl)-4-(2-hydroxyethyl)piperidine | HCID 854140 | — |
| 촉매 | Copper Sulfate | HCID 24462 | — |
| 용매 | Diethyl Ether | HCID 3283 | — |
| 용매 | Acetonitrile | HCID 6342 | — |
| 용매 | Sodium chloride; water | HCID 57417360 | — |
| 생성물 | Tert-butyl 4-(2-iodoethyl)piperidine-1-carboxylate | HCID 9974426 | — |
반응 단계
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.
출처 및 근거
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 특허 번호 | US06358979B1 |
|---|
| 출처 데이터셋 | uspto-grants-2002_03 |
|---|
| ORD ID | ord-c83c962e4a924518a69d95c326d2625c |
|---|
| 출처 메모 | uspto-grants-2002_03 |
|---|
