反応式
[N:1]1([C:7]([O:9][C:10]([CH3:13])(C)C)=[O:8])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.I[C:15]1[CH:19]=[CH:18][S:17][CH:16]=1.[CH3:20][C:21](C)([O-])C.[Na+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1>C1(C)C=CC=CC=1.O>[S:17]1[CH:18]=[CH:19][C:15]([N:4]2[CH2:3][CH2:2][N:1]([C:7]([O:9][CH2:10][CH2:13][CH2:20][CH3:21])=[O:8])[CH2:6][CH2:5]2)=[CH:16]1参加物
反応条件
- 温度
- 100 °C
実験手順
To a solution of tert-butyl piperazine-1-carboxylate (0.300 g, 1.61 mmol) in 10 mL of toluene under an atmosphere of nitrogen was added 3-iodothiophene (0.390 g, 1.86 mmol), sodium tert-butoxide (0.310 g, 3.22 mmol), tris (dibenzylidenacetone)palladium (0) (0.295 g, 0.322 mmol), and 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (X-Phos, 0.307 g, 0.644 mmol). The mixture was heated to 100° C. for 18 h, cooled to rt, and treated with water. The solution was extracted 3× with ethyl acetate, and the combined organic solution was washed with brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The resultant residue was purified via silica gel chromatography, eluting with 0-70% ethyl acetate, to provide text-butyl 4-(3-thienyl)piperazine-1-carboxylate that gave a proton NMR spectra consistent with theory.
後処理
- temperaturecooled to rt
- extractionThe solution was extracted 3× with ethyl acetate
- washthe combined organic solution was washed with brine
- dry with materialdried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe resultant residue was purified via silica gel chromatography
- washeluting with 0-70% ethyl acetate
出典と根拠
- ORDレコード
- ord-614555e96b724d83b2a7fb7b81e7bf0b
- 出典データセット
- uspto-grants-2013_02
- 特許番号
- US08383638B2
関連ノート
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