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碘化钠 → 5-(4-Fluorobenzyl)-3-oxo-1-oxa-4,9-diaza-spiro[5.5]undecane-9-carboxylic acid benzyl ester
参与物
| 角色 | 名称 | HCID | 投料 |
|---|---|---|---|
| 反应物 | 碘化钠 | HCID 5238 | — |
| 反应物 | 氯乙酰氯 | HCID 6577 | — |
| 反应物 | 碘化油 | HCID 30165 | — |
| 反应物 | 2-Methylpropan-2-olate | HCID 4574913 | — |
| 反应物 | 4-[1-Amino-2-(4-fluorophenyl)-ethyl]-4-hydroxypiperidine-1-carboxylic acid benzyl ester | HCID 57458014 | — |
| 产物 | 5-(4-Fluorobenzyl)-3-oxo-1-oxa-4,9-diaza-spiro[5.5]undecane-9-carboxylic acid benzyl ester | HCID 67527407 | 19% |
反应步骤
The title compound was prepared from aminoalcohol 103NLS28 (303 mg, 0.81 mmol) according to literature procedures (Clark et al., J. Med. Chem. 26:855-861 (1983)), by acylation of the amino function with chloroacetylchloride, followed by halogen exchange with NaI and ring closure of the iodide derivative in presence of tert-butoxide. Purification of the crude product by silica gel column chromatography, eluting with a stepwise gradient of 0-100% ethyl acetate in n-heptane, afforded the title compound (64 mg, 19% overall yield) as a colourless solid.
来源与证据
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 专利号 | US07727999B2 |
| 来源数据集 | uspto-grants-2010_06 |
| ORD ID | ord-4ff04c5e94c1429fb6e2c8b432ea5d8a |
| 来源说明 | uspto-grants-2010_06 |