Alpha-Aminoadipic Acid → n,6-Diacetyl-piperidin-2-one

HRID 1907062ノート

反応式

HRID 1907062 の反応式
[NH2:1][CH:2]([CH2:6][CH2:7][CH2:8][C:9]([OH:11])=O)[C:3]([OH:5])=O.[C:12](OC(=O)C)(=[O:14])[CH3:13].[CH2:19](N(CC)CC)C>CN(C1C=CN=CC=1)C>[C:12]([N:1]1[CH:2]([C:3](=[O:5])[CH3:19])[CH2:6][CH2:7][CH2:8][C:9]1=[O:11])(=[O:14])[CH3:13]

参加物

5

反応物 3

HCID 469Alpha-Aminoadipic AcidHCID 7918Acetic AnhydrideHCID 8471Triethylamine

生成物 1

HCID 67289323n,6-Diacetyl-piperidin-2-one

試薬・触媒・溶媒 1

HCID 142844-(Dimethylamino)pyridine触媒

反応条件

温度
60 °C

実験手順

A 50-mL round bottom flask is charged with racemic 2-aminoadipic acid (2.3 g, 1.43×10−3 mol) and triethylamine (7.5 mL), acetic anhydride (7.5 mL), and a catalytic amount of DMAP (15 mg). The mixture is heated to 60° C. for 24 h; the progress of the reaction is followed by TLC (eluent: ethyl acetate/petroleum ether, 8/2). Once the reaction is complete, the crude reaction product is concentrated as much as possible (rotary evaporator and vane pump) and then washed with water (5×20 mL). The water washings are extracted with CH2Cl2 (2×20 mL). The organic layers are combined and concentrated. Purification of 8 is carried out on a silica gel column (eluent: ethyl acetate/petroleum ether, 8/2). The fractions are dried, concentrated and the product crystallized in the form of pale yellow flakes.

後処理

  1. customthe crude reaction product
  2. concentrationis concentrated as
  3. custommuch as possible (rotary evaporator and vane pump)
  4. washwashed with water (5×20 mL)
  5. extractionThe water washings are extracted with CH2Cl2 (2×20 mL)
  6. concentrationconcentrated
  7. customPurification of 8
  8. customThe fractions are dried
  9. concentrationconcentrated
  10. customthe product crystallized in the form of pale yellow flakes

出典と根拠

ORDレコード
ord-ebbeb5a3f0654a4391d3adacf6daeca0
出典データセット
uspto-grants-2013_12
特許番号
US08597706B2

反応ノート

読み込み中…