Water → methyl 6-[(R)-3-[(R)-1-(naphthalen-1-yl)ethylamino]pyrrolidin-1-yl]-4-trifluoromethylnicotinate

HRID 2367942

反応式

HRID 2367942 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[C:22]1[CH:31]=[C:30]([C:32]([F:35])([F:34])[F:33])[C:25]([C:26]([O:28][CH3:29])=[O:27])=[CH:24][N:23]=1.C(=O)([O-])[O-].[K+].[K+].O>O1CCOCC1.C(OCC)(=O)C>[C:3]1([C@H:13]([NH:15][C@@H:16]2[CH2:20][CH2:19][N:18]([C:22]3[CH:31]=[C:30]([C:32]([F:33])([F:35])[F:34])[C:25]([C:26]([O:28][CH3:29])=[O:27])=[CH:24][N:23]=3)[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

参加物

7

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 2775340Methyl 6-chloro-4-(trifluoromethyl)nicotinateHCID 67407230(R)-3-[(R)-1-(naphthalen-1-yl)ethylamino]pyrrolidine dihydrochloride

生成物 1

HCID 58973503methyl 6-[(R)-3-[(R)-1-(naphthalen-1-yl)ethylamino]pyrrolidin-1-yl]-4-trifluoromethylnicotinate

試薬・触媒・溶媒 2

HCID 8857Ethyl Acetate溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

To a solution of 157 mg of (R)-3-[(R)-1-(naphthalen-1-yl)ethylamino]pyrrolidine dihydrochloride and 120 mg of methyl 6-chloro-4-(trifluoromethyl)-nicotinate in 5 ml of dioxane was added 346 mg of potassium carbonate, and the reaction solution was stirred at 100° C. for 1 day. Further, to the reaction mixture was irradiated at 140° C. for 1 hour by using a Microwave reaction system, and then, the reaction mixture was cooled to room temperature. To the mixture were added water and ethyl acetate, and the mixture was stirred and the liquids were separated. The organic layer was dried and concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=80:20→50:50), and then, purified by NH thin layer silica gel column chromatography (hexane:ethyl acetate=67:33) to obtain methyl 6-[(R)-3-[(R)-1-(naphthalen-1-yl)ethylamino]pyrrolidin-1-yl]-4-trifluoromethylnicotinate (the following Table, Example, 12.001).

後処理

  1. customFurther, to the reaction mixture was irradiated at 140° C. for 1 hour
  2. customa Microwave reaction system
  3. temperaturethe reaction mixture was cooled to room temperature
  4. stirringthe mixture was stirred
  5. customthe liquids were separated
  6. customThe organic layer was dried
  7. concentrationconcentrated under reduced pressure
  8. customthe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=80:20→50:50)
  9. custompurified by NH thin layer silica gel column chromatography (hexane:ethyl acetate=67:33)

出典と根拠

ORDレコード
ord-abc0552d8d4c49a7bfcc06f17258f455
出典データセット
uspto-grants-2014_04
特許番号
US08703721B2

関連ノート

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