Diisopropylamine → HCID 86629994、化合物

HRID 656464ノート

反応式

HRID 656464 の反応式
C(NC(C)C)(C)C.C([Li])CCC.[CH2:13]([N:20]1[CH:25]([C:26]#[N:27])[CH2:24][CH2:23][CH2:22][CH:21]1[C:28]#[N:29])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.CN(C)P(=O)(N(C)C)N(C)C.Br[CH2:42][C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44]>O1CCCC1>[CH2:13]([N:20]1[CH:25]([C:26]#[N:27])[CH2:24][CH2:23][CH2:22][C:21]1([CH2:42][C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44])[C:28]#[N:29])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

参加物

7

反応物 5

HCID 7912DiisopropylamineHCID 12679HexamethylphosphoramideHCID 79177tert-Butyl bromoacetateHCID 1767161-Benzylpiperidine-2,6-dicarbonitrileHCID 178418339Butyllithium

生成物 1

HCID 86629994HCID 86629994、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

反応条件

温度
-20 °C

実験手順

A solution of 378.000 mmol of diisopropylamine in 180 ml of tetrahydrofuran is admixed dropwise at −78° C. with 179.000 mmol of n-butyllithium (1.6M in hexane). The yellowish solution is stirred at −20° C. for 30 minutes then cooled again to −78° C. This solution is admixed dropwise at −78° C. with a solution of 126.000 mmol of 1-benzylpiperidine-2,6-dicarbonitrile [98195-08-5] and 138.600 mmol of hexamethylphosphorictriamide in 50 ml of tetrahydrofuran. The mixture is subsequently stirred at this temperature for 30 minutes. Then a solution of 130.000 mmol of tert-butyl bromoacetate in 50 ml of tetrahydrofuran is added dropwise. The mixture is subsequently stirred at −78° C. for an hour, the cold bath is removed, and the temperature is allowed to increase slowly overnight to room temperature. The reaction mixture is admixed with aqueous saturated ammonium chloride solution, the organic phase is separated off and the aqueous phase is extracted repeatedly with diethyl ether. The combined organic phases are washed with water and brine, dried with sodium sulphate and evaporated. From the residue the title compound is obtained by means of flash chromatography (SiO2 60 F) and identified on the basis of the Rf value.

後処理

  1. temperaturethen cooled again to −78° C
  2. stirringThe mixture is subsequently stirred at this temperature for 30 minutes
  3. stirringThe mixture is subsequently stirred at −78° C. for an hour
  4. customthe cold bath is removed
  5. temperatureto increase slowly overnight to room temperature
  6. customthe organic phase is separated off
  7. extractionthe aqueous phase is extracted repeatedly with diethyl ether
  8. washThe combined organic phases are washed with water and brine
  9. dry with materialdried with sodium sulphate
  10. customevaporated

出典と根拠

ORDレコード
ord-017280aeed7640c4a73a189a8b1998d5
出典データセット
uspto-grants-2011_12
特許番号
US08071773B2

反応ノート

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