Potassium Carbonate → HCID 60587666, compound

HRID 1804618Notes

Reaction equation

HRID 1804618 reaction equation
[N:1]1([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].Br[CH:21]1[CH2:25][CH2:24][O:23][C:22]1=[O:26]>CN(C)C=O>[O:26]=[C:22]1[CH:21]([N:4]2[CH2:5][CH2:6][N:1]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:2][CH2:3]2)[CH2:25][CH2:24][O:23]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 954632(3H)-Furanone, 3-bromodihydro-HCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 60587666HCID 60587666, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 2.0 g (11 mmol) of tert-butyl piperazine-1-carboxylate in 30 mL of anhydrous N,N-dimethylformamide was added 1.9 g (14 mmol) of potassium carbonate followed by 0.09 mL (11 mmol) of 3-bromodihydrofuran-2(3H)-one. The resulting heterogeneous mixture was stirred at ambient temperature of 12 h, quenched with water, then extracted with ethyl acetate. The combined organic layers were washed with water then brine, dried over magnesium sulfate and evaporated to dryness in vacuo. The residue was purified by silica gel chromatography eluting with a 0-75% acetone in hexanes gradient to afford the title compound as clear gum (2.2 g, 75%). LC-MS: m/z (ES) 271.2 (MH)+.

Workup

  1. customquenched with water
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layers were washed with water
  4. dry with materialbrine, dried over magnesium sulfate
  5. customevaporated to dryness in vacuo
  6. customThe residue was purified by silica gel chromatography
  7. washeluting with a 0-75% acetone in hexanes gradient

Sources & evidence

ORD record
ord-d231889ec36e4c8b83ff186e54c35c21
Source dataset
uspto-grants-2013_01
Patent number
US08354403B2

Reaction notes

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