Diethyl (cyanomethyl)phosphonate → HCID 67054970, compound

HRID 1772764Notes

Reaction equation

HRID 1772764 reaction equation
CC(C)([O-])C.[K+].[C:7]([CH2:9]P(=O)(OCC)OCC)#[N:8].O=[CH:19][CH2:20][N:21]1[CH2:26][CH2:25][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:23][CH2:22]1>C1COCC1>[C:7](/[CH:9]=[CH:19]/[CH2:20][N:21]1[CH2:26][CH2:25][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:23][CH2:22]1)#[N:8]

Participants

5

Reactant 3

HCID 75676Diethyl (cyanomethyl)phosphonateHCID 16737781tert-Butyl 4-(2-oxoethyl)piperazine-1-carboxylateHCID 23665647Potassium tert-butoxide

Product 1

HCID 67054970HCID 67054970, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a solution of 1 M of potassium tert-butoxide in THF (45.5 mL, 0.0455 mol) at 0° C. was added drop wise a solution of diethyl cyanomethylphosphonate (7.72 mL, 0.0477 mol) in THF (70 mL). The reaction mixture was warmed up to at RT, cooled to 0° C. again, and a solution of tert-butyl 4-(2-oxoethyl)piperazine-1-carboxylate (9.90 g, 0.0434 mol) in THF (10 mL) was added. The reaction mixture was allowed to warm up to RT and stirred for 2 more hours. After being quenched with water, the mixture was extracted with EtOAc. The organic layers were dried and concentrated. The residue was purified by silica gel column eluting with DCM to give the desired product (7.5 g, 69%).

Workup

  1. temperaturecooled to 0° C. again
  2. temperatureto warm up to RT
  3. customAfter being quenched with water
  4. extractionthe mixture was extracted with EtOAc
  5. customThe organic layers were dried
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column
  8. washeluting with DCM

Sources & evidence

ORD record
ord-258220abcdf54e5b94b49436ec754af6
Source dataset
uspto-grants-2016_02
Patent number
US09249145B2

Reaction notes

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