2-Allylamino-1-(3-(s)-hydroxy-pyrrolidin-1-yl)-2-(s)-phenyl-ethanone → HCID 20756538、化合物

HRID 23587ノート

反応式

HRID 23587 の反応式
[CH2:1]([NH:4][C@@H:5]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:6]([N:8]1[CH2:12][CH2:11][C@H:10]([OH:13])[CH2:9]1)=O)[CH:2]=[CH2:3].[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH2:1]([NH:4][C@@H:5]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:6][N:8]1[CH2:12][CH2:11][C@H:10]([OH:13])[CH2:9]1)[CH:2]=[CH2:3]

参加物

4

反応物 2

HCID 207565392-Allylamino-1-(3-(s)-hydroxy-pyrrolidin-1-yl)-2-(s)-phenyl-ethanoneHCID 21226445Aluminium lithium hydride

生成物 1

HCID 20756538HCID 20756538、化合物収率 68.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a stirred solution of 2-allylamino-1-(3-(S)-hydroxy-pyrrolidin-1-yl)-2-(S)-phenyl-ethanone (5.65 g, 15.1 mmol) in anhydrous tetrahydrofuran (60 cm3) cooled to 0° C. in an ice bath was added a 1 M solution of lithium aluminum hydride (22.6 cm3, 22.7 mmol) over 20 minutes. The solution was allowed to warm and stir at ambient temperature for 16 hours. The reaction was cooled to 0° C. in an ice bath and quenched with water (0.860 cm3), 15% sodium hydroxide (0.860 cm3) and water (2.60 cm3) to form a white flocculate precipitate. The mixture was vacuum filtered, the precipitate washed with tetrahydrofuran (5×30 cm3) and the filtrate volatile fractions removed in vacuo to afford a crude yellow oil. The crude product was purified by column chromatography (silica, eluting with dichloromethane-methanol-ammonium hydroxide 97:3:0 to 90:10:1) to afford the title compound as a yellow viscous oil (2.54 g, 68.3%) with a positive ion ESI (M+H)+247.2.

後処理

  1. temperatureto warm
  2. temperatureThe reaction was cooled to 0° C. in an ice bath
  3. customquenched with water (0.860 cm3), 15% sodium hydroxide (0.860 cm3) and water (2.60 cm3)
  4. customto form a white flocculate precipitate
  5. filtrationfiltered
  6. washthe precipitate washed with tetrahydrofuran (5×30 cm3)
  7. customthe filtrate volatile fractions removed in vacuo
  8. customto afford a crude yellow oil
  9. customThe crude product was purified by column chromatography (silica, eluting with dichloromethane-methanol-ammonium hydroxide 97:3:0 to 90:10:1)

出典と根拠

ORDレコード
ord-610a9013493f4ad29eda5f303f2c0eda
出典データセット
uspto-grants-2005_02
特許番号
US06852713B2

反応ノート

読み込み中…