4-Methylmorpholine → HCID 58882158, compound

HRID 2375308Notes

Reaction equation

HRID 2375308 reaction equation
[C:1]1(=[O:8])[O:7][C:5](=O)[CH2:4][O:3][CH2:2]1.[C:9]([O:13][C:14](=[O:20])[NH:15][CH2:16][CH2:17][CH2:18][NH2:19])([CH3:12])([CH3:11])[CH3:10].CN1CCOCC1>CC(N(C)C)=O.CCOC(C)=O>[C:9]([O:13][C:14](=[O:20])[NH:15][CH2:16][CH2:17][CH2:18][N:19]1[C:1](=[O:8])[CH2:2][O:3][CH2:4][C:5]1=[O:7])([CH3:12])([CH3:10])[CH3:11]

Participants

6

Reactant 3

HCID 79724-MethylmorpholineHCID 782321,4-Dioxane-2,6-dioneHCID 2735700tert-Butyl (3-aminopropyl)carbamate

Product 1

HCID 58882158HCID 58882158, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of diglycolic anhydride (22 g, 0.188 mol), tert-butyl-3-aminopropylcarbamate (65 g, 0.377 mol) and NMM (21 mL, 0.188 mol) in DMA (300 mL) was heated up to 120° C. for 48 h. The reaction mixture was cooled down to r.t and diluted with EtOAc (1.5 L). The solution was washed with brine (5×150 mL), dried with MgSO4 and concentrated under reduced pressure. The crude was purified by column chromatography over silica gel (15% ethylacetate in chloroform) affording 15 g of the title compound (30%).

Workup

  1. temperatureThe reaction mixture was cooled down
  2. washThe solution was washed with brine (5×150 mL)
  3. dry with materialdried with MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe crude was purified by column chromatography over silica gel (15% ethylacetate in chloroform)

Sources & evidence

ORD record
ord-ef4caa2fec0944d5b524b02fd3c6da9d
Source dataset
uspto-grants-2008_12
Patent number
US07465736B2

Reaction notes

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