N,N-Dimethylaniline → HCID 15927742, compound

HRID 2408328Notes

Reaction equation

HRID 2408328 reaction equation
[CH:1]1([OH:5])[CH2:4][CH2:3][CH2:2]1.CN(C)C1C=CC=CC=1.ClC(Cl)(O[C:19](=[O:25])[O:20]C(Cl)(Cl)Cl)Cl.O[N:28]1[C:32](=[O:33])[CH2:31][CH2:30][C:29]1=[O:34]>C1COCC1.C(Cl)Cl.O>[C:19](=[O:25])([O:20][N:28]1[C:32](=[O:33])[CH2:31][CH2:30][C:29]1=[O:34])[O:5][CH:1]1[CH2:4][CH2:3][CH2:2]1

Participants

8

Reactant 4

HCID 949N,N-DimethylanilineHCID 76218CyclobutanolHCID 80170N-HydroxysuccinimideHCID 94429Triphosgene

Product 1

HCID 15927742HCID 15927742, compoundYield 16.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
10 °C

Procedure

Cyclobutanol (2 g, 27.7 mmol) and N,N-Dimethylaniline (3.69 g, 30.5 mmol) were slowly added to a mixture of triphosgene (8.22 g, 27.7 mmol, 1 eq) in dry THF (20 mL) at 0° C. After 10 minutes, the reaction was warmed to 10° C. and stirred for 12 hour. Dry CH2Cl2 (20 mL) was added and the mixture was poured slowly into a solution of N-hydroxysuccinimide (4.14 g, 36 mmol) in dry CH2Cl2 (20 mL) at 0° C. The mixture was stirred at 10° C. for 10 hours. H2O (20 mL) was added and the mixture was stirred for 3 hours. The mixture was extracted with ethyl acetate (2×30 mL). The organic layer was washed with brine (20 mL) and dried over Na2SO4. The solvent was removed under vacuum resulting in cyclobutyl 2,5-dioxopyrrolidin-1-yl carbonate (1 g, 16% yield).

Workup

  1. stirringThe mixture was stirred at 10° C. for 10 hours
  2. stirringthe mixture was stirred for 3 hours
  3. extractionThe mixture was extracted with ethyl acetate (2×30 mL)
  4. washThe organic layer was washed with brine (20 mL)
  5. dry with materialdried over Na2SO4
  6. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-ac551a94d3564c3dbed418a80448d69f
Source dataset
uspto-grants-2014_08
Patent number
US08815849B2

Reaction notes

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