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tert-butyl (2R,3S)-6-oxo-2,3-diphenylmorpholine-4-carboxylate → tert-butyl (2R, 3S, 5S)-6-oxo-2,3-diphenyl-5-(3-tert-butyl-4-((tert-butyldimethylsilyl)oxy)benzyl)-4-morpholinecarboxylate
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | tert-butyl (2R,3S)-6-oxo-2,3-diphenylmorpholine-4-carboxylate | HCID 981230 | — |
| 反応物 | Sodium bis(trimethylsilyl)amide | HCID 2724254 | — |
| 反応物 | 3-Tert-butyl-4-((tert-butyldimethylsilyl)oxy)benzyl bromide | HCID 18352495 | — |
| 溶媒 | Tetrahydrofuran | HCID 8028 | — |
| 生成物 | tert-butyl (2R, 3S, 5S)-6-oxo-2,3-diphenyl-5-(3-tert-butyl-4-((tert-butyldimethylsilyl)oxy)benzyl)-4-morpholinecarboxylate | HCID 57296200 | 71.3% |
反応手順
According to example 142, 3.82 g of tert-butyl (2R, 3S)-(-)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate was alkylated with 3.86 g of 3-tert-butyl-4-((tert-butyldimethylsilyl)oxy)benzyl bromide in 80 mL of anhydrous THF using 11.34 mL of 1 M sodium bis(trimethylsilyl)amide in THF. The crude product was subjected to flash chromatography on silica gel (85:15 hexane:EtOAc) to afford 4.85 g (71%) of tert-butyl (2R, 3S, 5S)-6-oxo-2,3-diphenyl-5-(3-tert-butyl-4-((tert-butyldimethylsilyl)oxy)benzyl)-4-morpholinecarboxylate as a white foam, m.p. 75-83° C.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US06140100 |
| 出典データセット | uspto-grants-2000_10 |
| ORD ID | ord-4cf691fcca5d4b6e8b8446acc3212b0b |
| 出典メモ | uspto-grants-2000_10 |