Potassium Carbonate → (R)-1-(3-chloropyrazin-2-yl)pyrrolidin-3-yl-[(R)-1-(naphthalen-1-yl)ethyl]amine

HRID 1811620

反応式

HRID 1811620 の反応式
Cl.Cl.[C:3]1([C@H:13]([NH:15][C@@H:16]2[CH2:20][CH2:19][NH:18][CH2:17]2)[CH3:14])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1.[Cl:21][C:22]1[C:27](Cl)=[N:26][CH:25]=[CH:24][N:23]=1.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[Cl:21][C:22]1[C:27]([N:18]2[CH2:19][CH2:20][C@@H:16]([NH:15][C@@H:13]([C:3]3[C:12]4[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=4)[CH:6]=[CH:5][CH:4]=3)[CH3:14])[CH2:17]2)=[N:26][CH:25]=[CH:24][N:23]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 785752,3-DichloropyrazineHCID 67407230(R)-3-[(R)-1-(naphthalen-1-yl)ethylamino]pyrrolidine dihydrochloride

生成物 1

HCID 58973557(R)-1-(3-chloropyrazin-2-yl)pyrrolidin-3-yl-[(R)-1-(naphthalen-1-yl)ethyl]amine収率 35.1%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To a solution of 162 mg of (R)-3-[(R)-1-(naphthalen-1-yl)ethylamino]pyrrolidine dihydrochloride and 79.0 mg of 2,3-dichloro-pyrazine in 5 ml of ethanol was added 345 mg of potassium carbonate, and the mixture was stirred under reflux for 16 hours. The reaction mixture was filtered, and the solvent was evaporated, and to the residue was added a saturated aqueous sodium bicarbonate solution and chloroform, and the liquids were separated. The organic layer was dried, and the solvent was evaporated, then, the residue was purified by NH silica gel column chromatography (hexane:ethyl acetate=97:3→80:20) and by silica gel chromatography (hexane:ethyl acetate=90:10→0:100) to obtain 64.0 mg of (R)-1-(3-chloropyrazin-2-yl)pyrrolidin-3-yl-[(R)-1-(naphthalen-1-yl)ethyl]amine. (2) In 2 ml of chloroform was dissolved 64.0 mg of (R)-1-(3-chloropyrazin-2-yl)pyrrolidin-3-yl-[(R)-1-(naphthalen-1-yl)ethyl]amine, and 3 ml of a solution of 4M hydrochloric acid in dioxane was added to the mixture, and the resulting mixture was stirred. After the reaction mixture was concentrated under reduced pressure, diethyl ether was added to the residue, and the precipitates were collected by filtration, washed with diethyl ether, and dried to obtain 63.9 mg of (R)-1-(3-chloropyrazin-2-yl)pyrrolidin-3-yl-[(R)-1-(naphthalen-1-yl)ethyl]amine dihydrochloride (the following Table A2, Example 2.001).

後処理

  1. temperatureunder reflux for 16 hours
  2. filtrationThe reaction mixture was filtered
  3. customthe solvent was evaporated
  4. additionto the residue was added a saturated aqueous sodium bicarbonate solution and chloroform
  5. customthe liquids were separated
  6. customThe organic layer was dried
  7. customthe solvent was evaporated
  8. customthe residue was purified by NH silica gel column chromatography (hexane:ethyl acetate=97:3→80:20) and by silica gel chromatography (hexane:ethyl acetate=90:10→0:100)

出典と根拠

ORDレコード
ord-c088658354454ea79920b80a5072ea6e
出典データセット
uspto-grants-2013_01
特許番号
US08362274B2

関連ノート

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