Cyanide → 1,1'-Bipiperidine
反応式
[C-:1]#[N:2].C[Mg+].[Br-].[CH2:6]1[CH2:10]O[CH2:8][CH2:7]1>CCOCC>[N:2]1([N:2]2[CH2:1][CH2:10][CH2:6][CH2:7][CH2:8]2)[CH2:1][CH2:10][CH2:6][CH2:7][CH2:8]1参加物
5
反応条件
- 温度
- 25 °C
実験手順
The cyanide (4.87 g, 15 mmol) was taken up in THF (75 ml). CH3MgBr (25 ml of a 3.0 M solution in Et2O) was added to the reaction mixture at 0° C. The solution was allowed to warm to 25° C. and was stirred at that temperature for 18 h. The solution was partitioned between 25 wt % aqueous solution of sodium citrate and EtOAc. The aqueous layer was extracted with EtOAc. The combined EtOAc layers were washed with brine and dried (Na2SO4). Filtration and concentration gave a yellow oil. Purification via flash chromatography (95/5 to 90/10 EtOAc/MeOH. SiO2) gave 3.7 g (79%) of the piperidino-piperidine 12 as a yellow gum. Step 2:
後処理
- customThe solution was partitioned between 25 wt % aqueous solution of sodium citrate and EtOAc
- extractionThe aqueous layer was extracted with EtOAc
- washThe combined EtOAc layers were washed with brine
- dry with materialdried (Na2SO4)
- filtrationFiltration and concentration
- customgave a yellow oil
- customPurification via flash chromatography (95/5 to 90/10 EtOAc/MeOH. SiO2)
出典と根拠
- ORDレコード
- ord-4a655482062641e7bc8fd07e1bcca2ca
- 出典データセット
- uspto-grants-2006_03
- 特許番号
- US07008946B2
反応ノート
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