Alpha-Aminoadipic Acid → n,6-Diacetyl-piperidin-2-one
Reaction equation
[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]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
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.
Workup
- customthe crude reaction product
- concentrationis concentrated as
- custommuch as possible (rotary evaporator and vane pump)
- washwashed with water (5×20 mL)
- extractionThe water washings are extracted with CH2Cl2 (2×20 mL)
- concentrationconcentrated
- customPurification of 8
- customThe fractions are dried
- concentrationconcentrated
- customthe product crystallized in the form of pale yellow flakes
Sources & evidence
- ORD record
- ord-ebbeb5a3f0654a4391d3adacf6daeca0
- Source dataset
- uspto-grants-2013_12
- Patent number
- US08597706B2
Reaction notes
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