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

HRID 358350노트

반응식

HRID 358350 반응식
[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]

참가 물질

5

반응물 3

HCID 311Citric AcidHCID 12461845HCID 12461845, 화합물HCID 21225700Diisobutylaluminumhydride

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매2회

반응 조건

온도
-20 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-25ce91b5c79a4fa398891de48b3cdf82
출처 데이터셋
uspto-grants-1984_08
특허 번호
US04466976

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