Citric Acid → 5H-Pyrrolizine, 6,7-dihydro-1-formyl

HRID 358350ノート

反応式

HRID 358350 の反応式
[C:1]([C:3]1[CH:4]=[CH:5][N:6]2[C:10]=1[CH2:9][CH2:8][CH2:7]2)#N.[H-].C([Al+]CC(C)C)C(C)C.C(O)(=O)CC(CC(O)=O)(C(O)=O)[OH:24]>C1(C)C=CC=CC=1>[CH:1]([C:3]1[CH:4]=[CH:5][N:6]2[C:10]=1[CH2:9][CH2:8][CH2:7]2)=[O:24]

参加物

5

反応物 3

HCID 311Citric AcidHCID 12461845HCID 12461845、化合物HCID 21225700Diisobutylaluminumhydride

生成物 1

HCID 2140555H-Pyrrolizine, 6,7-dihydro-1-formyl収率 59%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒2 回

反応条件

温度
-20 °C

実験手順

13.21 g (0.1 mol) of 7-cyano-2,3-dihydro-1H-pyrrolizine is dissolved in 150 ml of absolute toluene and cooled to -20° C. To this solution is added dropwise 108 ml (0.13 mol) of a 1.2-molar diisobutyl aluminum hydride solution in toluene; the mixture is then warmed to room temperature, stirred for another hour, and decomposed with 300 ml of 10% aqueous citric acid solution. The product is extracted with methylene chloride, the organic phase is dried, concentrated, and the residue recrystallized from ether, thus obtaining 8.0 g (59% of theory) of 7-formyl-2,3-dihydro-1H-pyrrolizine, mp 58° C.

後処理

  1. temperaturethe mixture is then warmed to room temperature
  2. extractionThe product is extracted with methylene chloride
  3. customthe organic phase is dried
  4. concentrationconcentrated
  5. customthe residue recrystallized from ether

出典と根拠

ORDレコード
ord-25ce91b5c79a4fa398891de48b3cdf82
出典データセット
uspto-grants-1984_08
特許番号
US04466976

反応ノート

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