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N-(tert-Butoxycarbonyl)-D-prolinal → tert-butyl (R)-2-[(E)-2-(3-chlorophenyl)vinyl]pyrrolidine-1-carboxylate
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | N-(tert-Butoxycarbonyl)-D-prolinal | HCID 7009153 | — |
| 反応物 | Diethyl ((3-chlorophenyl)methyl)phosphonate | HCID 10106792 | — |
| 反応物 | Lithium bis(trimethylsilyl)amide | HCID 57426343 | — |
| 溶媒 | Tetrahydrofuran | HCID 8028 | — |
| 生成物 | tert-butyl (R)-2-[(E)-2-(3-chlorophenyl)vinyl]pyrrolidine-1-carboxylate | HCID 58483903 | — |
反応手順
775 mg of commercially available diethyl 3-chlorobenzylphosphonate are dissolved in 20 ml of THF, and 3 ml of lithium hexamethyldisilazane are added dropwise at −78° C. under protective gas. After 1 h, a solution of 500 mg of tert-butyl-(R)-2-formylpyrrolidine-1-carboxylate in 5 ml of THF is added dropwise at the temperature indicated. The batch is stirred at RT for 3 h and subsequently subjected to aqueous work-up, giving 1 g of tert-butyl (R)-2-[(E)-2-(3-chlorophenyl)vinyl]pyrrolidine-1-carboxylate as colourless oil, which is immediately reacted further.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US08846694B2 |
| 出典データセット | uspto-grants-2014_09 |
| ORD ID | ord-fcfd28a2209f4e4eae364783af707dc1 |
| 出典メモ | uspto-grants-2014_09 |