関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | Dimethyl Sulfide | HCID 1068 | — |
| 反応物 | Boron trifluoride etherate | HCID 8000 | — |
| 反応物 | Ammonium Hydroxide | HCID 14923 | — |
| 反応物 | Ammonium Chloride | HCID 25517 | — |
| 反応物 | benzyl 2-ethyl-4-oxo-3,4-dihydropyridine-1(2H)-carboxylate | HCID 53419195 | — |
| 反応物 | HCID 178478191 | HCID 178478191 | — |
| 溶媒 | Tetrahydrofuran | HCID 8028 | — |
| 生成物 | Benzyl 2-(4-chlorophenyl)-6-ethyl-4-oxopiperidine-1-carboxylate | HCID 59342384 | 33.3% |
反応手順
CuBr.SMe2 (5.6 g, 27.2 mmol) was added to dry THF (64 mL). It was cooled to −78° C. 4-Chlorophenylmagnesium bromide (27.2 mL, 1 M in THF, 27.2 mmol) was added to the mixture slowly over 1 hr at −78° C. Then BF3.Et2O (3.44 mL, 27.2 mmol) was added and the mixture was stirred for 5 min. Then ketone 82 (4 g, 8.1 mmol) in THF (55 mL) was added slowly over 1 hr at −78° C. After 2 hr stirring at −78° C., an aqueous solution of NH4Cl/conc. NH4OH (1:1, 20%, 60 mL) was added. The mixture was warmed to rt and extracted with EtOAc (200 mL×3), The combined organic layers were washed with brine, dried and concentrated to a residue and purified by silica gel chromatography (0-40% EtOAc/hexanes) to afford pure 83 (1 g, 2.7 mmol, 33%) as a mixture of cis stereoisomers.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 特許番号 | US07732609B2 |
|---|
| 出典データセット | uspto-grants-2010_06 |
|---|
| ORD ID | ord-7b77112cbcbd41cea3bf4f3c5c428bda |
|---|
| 出典メモ | uspto-grants-2010_06 |
|---|
