Cyanide → 1,1'-Bipiperidine

HRID 1743115

反応式

HRID 1743115 の反応式
[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

反応物 3

HCID 5975CyanideHCID 8028TetrahydrofuranHCID 178418689HCID 178418689、化合物

生成物 1

HCID 682791,1'-Bipiperidine収率 79%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

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

  1. customThe solution was partitioned between 25 wt % aqueous solution of sodium citrate and EtOAc
  2. extractionThe aqueous layer was extracted with EtOAc
  3. washThe combined EtOAc layers were washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationFiltration and concentration
  6. customgave a yellow oil
  7. 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

関連ノート

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