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Binap, (A+-)- → benzyl (1S,5S)-6-(5,6-dichloro-3-pyridinyl)-3,6-diazabicyclo[3.2.0]heptane-3-carboxylate
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Binap, (A+-)- | HCID 634876 | — |
| 反応物 | 2,3-Dichloro-5-iodopyridine | HCID 21892874 | — |
| 反応物 | benzyl (1S,5S)-3,6-diazabicyclo[3.2.0]heptane-3-carboxylate | HCID 23635906 | — |
| 反応物 | Sodium t-butoxide | HCID 23676156 | — |
| 触媒 | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| 生成物 | benzyl (1S,5S)-6-(5,6-dichloro-3-pyridinyl)-3,6-diazabicyclo[3.2.0]heptane-3-carboxylate | HCID 23636393 | 25% |
反応手順
The product of Example 52D (451 mg, 1.94 mmol) was coupled with 2,3-dichloro-5-iodopyridine (805 mg, 2.94 mmol; U.S. Pat. No. 7,733,912) using tris(dibenzylideneacetone)dipalladium (Pd2(dba)3, 36 mg, 0.039 mmol; Alfa Aesar), 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (BINAP, 82 mg, 0.13 mmol; Strem), and sodium tert-butoxide (360 mg, 3.75 mmol; Aldrich) according to the procedure described in Example 1E to provide the title compound (184 mg, 25% yield). MS (DCI/NH3) m/z 378, 380 (M+H)+.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US08119635B2 |
| 出典データセット | uspto-grants-2012_02 |
| ORD ID | ord-1ce4c1c5547748b3ab59ec427bc049b5 |
| 出典メモ | uspto-grants-2012_02 |