Potassium Cyanide → 1-[(RS)-1-Cyano-[(S)-1-(1-naphthyl)ethylamino]methyl]-1-ethoxycarbonylcyclopropane

HRID 342046

반응식

HRID 342046 반응식
[CH:1]([C:3]1([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:5][CH2:4]1)=O.[C:11]1([C@@H:21]([NH2:23])[CH3:22])[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][CH:12]=1.[C-:24]#[N:25].[K+].S([O-])(O)=O.[Na+]>C(O)C.O>[C:24]([CH:1]([NH:23][C@H:21]([C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][CH:12]=1)[CH3:22])[C:3]1([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:5][CH2:4]1)#[N:25]

참가 물질

7

반응물 4

HCID 9032Potassium CyanideHCID 663251-Naphthalenemethanamine, alpha-methyl-, (alphaS)-HCID 9964122Ethyl 1-formylcyclopropanecarboxylateHCID 23665763Sodium Bisulfite

생성물 1

HCID 153910541-[(RS)-1-Cyano-[(S)-1-(1-naphthyl)ethylamino]methyl]-1-ethoxycarbonylcyclopropane수율 72.2%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매

반응 조건

온도
50 °C

실험 절차

An eggplant type flask was charged with 426 mg of ethyl 1-formylcyclopropane-1-carboxylate to which were further added 771 mg of (S)-1-(1-naphthyl)ethylamine dissolved in 5 ml of ethanol, 293 mg of potassium cyanide dissolved in 2 ml of water and 937 mg of sodium hydrogen sulfite in that order at 0° C. The reaction system was stirred for 3.5 hours at 50° C. After confirming completion of the reaction, the reaction solution was mixed with ice water and extracted with ethyl acetate. Next, the resulting organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate and, after removing insoluble matter by filtration, the solvent was evaporated under a reduced pressure. Thereafter, the resulting residue was subjected to a silica gel column chromatography (hexane:ethyl acetate=5:1) to obtain 698 mg (72%) of a diastereomer mixture in the form of colorless oil. Formation ratio of the two diastereomers was calculated under the following analytical conditions.

후처리

  1. customat 0° C
  2. customcompletion of the reaction
  3. extractionextracted with ethyl acetate
  4. washNext, the resulting organic layer was washed with water and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customafter removing insoluble matter
  7. filtrationby filtration
  8. customthe solvent was evaporated under a reduced pressure

출처 및 근거

ORD 기록
ord-8a5d6db9e9b14ad998ba0ad650c1591d
출처 데이터셋
uspto-grants-1999_01
특허 번호
US05856518

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