関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | Triphenylphosphine | HCID 11776 | — |
| 反応物 | 4-Cyanophenol | HCID 13019 | — |
| 反応物 | 2-Methyl 1-(phenylmethyl) (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate | HCID 688411 | — |
| 反応物 | Diethyl azodicarboxylate | HCID 5462977 | — |
| 溶媒 | Tetrahydrofuran | HCID 8028 | — |
| 生成物 | N-carbobenzyloxy-4-(cis)-(4-cyanophenoxy)-L-proline methyl ester | HCID 18654599 | 89% |
反応手順
To a solution of N-carbobenzyloxy-trans-4-hydroxy-L-proline methyl ester (10.0 g, 35.8 mmol) in 200 mL of anhydrous THF under N2 was added triphenylphosphine (10.6 g, 39.4 mmol) and 4 -cyanophenol (4.7 g, 39.4 mmol). This solution was cooled to 0° C. and then treated with diethylazodicarboxylate (6.3 mL, 39.4 mmol), added dropwise over 30 minutes The reaction was warmed to room temperature and stirred for 2 days. The solvent was removed in vacuo and the residue chromatographed (SiO2, 30% ethyl acetate/hexanes) to provide 12.1 g (89%) of N-carbobenzyloxy-4-(cis)-(4-cyanophenoxy)-L-proline methyl ester as a colorless oil. MS.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 特許番号 | US05401851 |
|---|
| 出典データセット | uspto-grants-1995_03 |
|---|
| ORD ID | ord-1b82840bb2e342358fd6601cacdb9793 |
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| 出典メモ | uspto-grants-1995_03 |
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