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

HRID 342046

反応式

HRID 342046 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒

反応条件

温度
50 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-8a5d6db9e9b14ad998ba0ad650c1591d
出典データセット
uspto-grants-1999_01
特許番号
US05856518

関連ノート

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