海萝胶 → 1-[(RS)-1-Cyano-[(S)-1-phenylpropylamino]methyl]-1-ethoxycarbonylcyclopropane

HRID 342047

反应方程式

HRID 342047 反应方程式
[C-:1]#[N:2].[K+].[C:4]1([C@@H:10]([NH2:13])[CH2:11][CH3:12])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH:14]([C:16]1([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:18][CH2:17]1)=O.Cl>C(O)C.O>[C:1]([CH:14]([NH:13][C@H:10]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH2:11][CH3:12])[C:16]1([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:18][CH2:17]1)#[N:2]

参与物

7

反应物 4

HCID 313海萝胶HCID 9032氰化钾HCID 6993773(S)-(-)-1-苯丙胺HCID 99641221-甲酰基环丙烷-1-甲酸乙酯

产物 1

HCID 702112091-[(RS)-1-Cyano-[(S)-1-phenylpropylamino]methyl]-1-ethoxycarbonylcyclopropane收率 59.1%

试剂、催化剂与溶剂 2

HCID 702乙醇溶剂HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]溶剂

实验过程

An eggplant type flask was charged with 136 mg of potassium cyanide, 501 mg of (S)-1-phenylpropylamine and 1 ml of water. After adding 152 mg of ethyl 1-formylcyclopropane-1-carboxylate dissolved in 2 ml of ethanol, dropwise at room temperature, the resulting mixture was further mixed with 0.2 ml of concentrated hydrochloric acid, and stirred for 1 hour at the same temperature and then for 2 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=10:1) to obtain 181 mg (59%) of a diastereomer mixture in the form of colorless oil. Formation ratio of the two diastereomers was calculated under the following analytical conditions.

后处理

  1. waitfor 2 hours at 50° 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

来源与证据

ORD记录
ord-d5a95cc5e12c49ebb314619c0387ebd4
来源数据集
uspto-grants-1999_01
专利号
US05856518

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