Ethyl acetate hexane → (S)-2-(dibenzylamino)pentanal

HRID 1972326ノート

反応式

HRID 1972326 の反応式
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([N:14]([CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C@@H:15]([CH2:22][CH2:23][CH3:24])[C:16](N(OC)C)=[O:17])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(OCC)(=O)C.CCCCCC>O1CCCC1>[CH2:25]([N:14]([CH2:7][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C@@H:15]([CH2:22][CH2:23][CH3:24])[CH:16]=[O:17])[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

参加物

5

反応物 3

HCID 21226206Ethyl acetate hexaneHCID 21226445Aluminium lithium hydrideHCID 44223340(S)-2-(dibenzylamino)-N-methoxy-N-methylpentanamide

生成物 1

HCID 44223341(S)-2-(dibenzylamino)pentanal収率 94.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To anhydrous tetrahydrofuran (1.5 L) previously cooled to −20° C. to −30° C. was added solid lithium aluminum hydride (33.5 g; 0.882 mol; 120 mole %) slowly with stirring. A solution of (S)-2-(dibenzylamino)-N-methoxy-N-methylpentanamide (6) (250 g; 0.735 mol) in anhydrous tetrahydrofuran (1 L) at −30° C. was slowly added to the above mixture under a nitrogen atmosphere. The reaction was continued for 2 hours at −30° C., monitoring progress of the reaction by TLC analysis (ethyl acetate/hexane, 1:9). Upon completion of the reaction, the excess reagent was quenched by the dropwise addition of ethyl acetate (1 L) and ice-cold water (300 ml) at −30° C. The insoluble salts were filtered through celite, the filtrate diluted with water (3 L), and the product extracted into ethyl acetate (2 L). The combined ethyl acetate layers were washed with water (2 L), dried over sodium sulfate, filtered, and solvent removed under reduced pressure to provide (S)-2-(dibenzylamino)pentanal (7) (195 g) as a light yellow oil, which was used without purification in the next step.

後処理

  1. customUpon completion of the reaction
  2. customthe excess reagent was quenched by the dropwise addition of ethyl acetate (1 L) and ice-cold water (300 ml) at −30° C
  3. filtrationThe insoluble salts were filtered through celite
  4. additionthe filtrate diluted with water (3 L)
  5. extractionthe product extracted into ethyl acetate (2 L)
  6. washThe combined ethyl acetate layers were washed with water (2 L)
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. customsolvent removed under reduced pressure

出典と根拠

ORDレコード
ord-67e71df01f9d47fab65e284b8a710a68
出典データセット
uspto-grants-2013_04
特許番号
US08431733B2

反応ノート

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