Diethyl (cyanomethyl)phosphonate → HCID 68748229, compound

HRID 1257932Notes

Reaction equation

HRID 1257932 reaction equation
C[C:2]([CH3:5])([O-])C.[K+].[C:7]([CH2:9]P(=O)(OCC)OCC)#[N:8].O=[C:19]1[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])(C)C)=[O:26])[CH2:21][CH2:20]1>C1COCC1>[C:7]([CH:9]=[C:19]1[CH2:20][CH2:21][N:22]([C:25]([O:27][CH2:28][CH2:31][CH2:2][CH3:5])=[O:26])[CH2:23][CH2:24]1)#[N:8]

Participants

5

Reactant 3

HCID 75676Diethyl (cyanomethyl)phosphonateHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 23665647Potassium tert-butoxide

Product 1

HCID 68748229HCID 68748229, compoundYield 96.81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a solution of 1.0 M of potassium tert-butoxide in THF (26.3 mL) at 0° C. was added drop wise a solution of diethyl cyanomethylphosphonate (4.47 mL, 0.0276 mol) in THF (33.6 mL). The reaction was warmed to RT and then cooled at 0° C. again. To the reaction mixture was then added a solution of tert-butyl 4-oxo-1-piperidinecarboxylate (5.0 g, 0.025 mol) in THF (6.72 mL). The reaction was allowed to warm up to RT and stirred overnight. After being quenched with water, the mixture was extracted with EtOAc. The combined organic layers were washed with brine, dried, and concentrated. The crude mixture was purified on silica gel eluting with EtOAc in hexanes (0-60%) to give the desired product (5.4 g, 96.81%). LCMS: (M+Na)=244.9, (M−56+H)=167.0.

Workup

  1. temperaturecooled at 0° C. again
  2. temperatureto warm up to RT
  3. customAfter being quenched with water
  4. extractionthe mixture was extracted with EtOAc
  5. washThe combined organic layers were washed with brine
  6. customdried
  7. concentrationconcentrated
  8. customThe crude mixture was purified on silica gel eluting with EtOAc in hexanes (0-60%)

Sources & evidence

ORD record
ord-e3cdaf7c619e4c39818e28df147af216
Source dataset
uspto-grants-2013_06
Patent number
US08461330B2

Reaction notes

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