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Dimethyl Sulfoxide → tert-Butyl 1-oxa-6-azaspiro(2.5)octane-6-carboxylate
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Dimethyl Sulfoxide | HCID 679 | — |
| 反応物 | Sodium hydride | HCID 24758 | — |
| 反応物 | Sulfoxonium, trimethyl-, iodide (1:1) | HCID 74498 | — |
| 反応物 | tert-Butyl 4-oxopiperidine-1-carboxylate | HCID 735900 | — |
| 溶媒 | Water | HCID 962 | — |
| 溶媒 | Ethyl Acetate | HCID 8857 | — |
| 生成物 | tert-Butyl 1-oxa-6-azaspiro(2.5)octane-6-carboxylate | HCID 22135564 | 80.3% |
反応手順
55% sodium hydride (6.02 g) was added under ice-cooling to a DMSO (250 mL) suspension of trimethylsulfoxonium iodide (33.1 g), and stirring was performed at room temperature for 1 hour. A DMSO (125 ml) solution of tert-butyl 4-oxopiperidine-1-carboxylate (25.0 g) was added, and heated and stirred at 60° C. for 1 hour. Purified water was added to the mixture, and extraction was performed with EtOAc. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (EtOAc/hexane) to obtain tert-butyl 1-oxa-6-azaspiro[2.5]octane-6-carboxylate (21.5 g),
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US08822688B2 |
| 出典データセット | uspto-grants-2014_09 |
| ORD ID | ord-7a1082cecff047baad1b5aa5230fb810 |
| 出典メモ | uspto-grants-2014_09 |