Diethyl cyanophosphonate → HCID 68925513, compound

HRID 32098Notes

Reaction equation

HRID 32098 reaction equation
P([C:9]#[N:10])(OCC)(OCC)=O.[CH3:11][Si]([N-][Si](C)(C)C)(C)C.[Na+].[C:21]([O:25][C:26](=[O:40])[NH:27][CH:28]1[C:37]2[C:32](=[CH:33][C:34]([CH:38]=O)=[CH:35][CH:36]=2)[CH2:31][CH2:30][CH2:29]1)([CH3:24])([CH3:23])[CH3:22]>C1COCC1>[C:21]([O:25][C:26](=[O:40])[NH:27][CH:28]1[C:37]2[C:32](=[CH:33][C:34]([CH:38]=[CH:11][C:9]#[N:10])=[CH:35][CH:36]=2)[CH2:31][CH2:30][CH2:29]1)([CH3:24])([CH3:23])[CH3:22]

Participants

5

Reactant 3

HCID 76257Diethyl cyanophosphonateHCID 2724254Sodium bis(trimethylsilyl)amideHCID 58841363HCID 58841363, compound

Product 1

HCID 68925513HCID 68925513, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of diethyl cyanophosphate (6.62 g, 37.36 mmol) in dry THF (25 mL) at 0° C. was added sodium bis(trimethylsilyl)amide (32 mL, 32.03 mmol) dropwise via the addition funnel. The temp. was kept between 0° C. to 5° C. for 30 min. The resulting mixture was then cooled to −78° C. followed by adding (6-formyl-1,2,3,4-tetrahydro-naphthalen-1-yl)-carbamic acid tert-butyl ester (2.94 g, 10.67 mmol) in THF (40 mL) dropwise via the addition funnel. After the addition, it was stirred for 18 h and slowly warmed to RT. The reaction mixture was quenched with sat. NH4Cl. Solvent was removed. The residue was partitioned between EtOAc and water. The organic layer was washed with water, brine, dried over MgSO4 and evaporated in vacuo. The crude product was purified by chromatography on silica gel. Elution with Hex:EtOAc mixture (85:15) gave final compound MS m/z: 299.12 (M+H). Calc'd. for C18H22N2O2-298.38.

Workup

  1. additionAfter the addition, it
  2. temperatureslowly warmed to RT
  3. customThe reaction mixture was quenched with sat. NH4Cl
  4. customSolvent was removed
  5. customThe residue was partitioned between EtOAc and water
  6. washThe organic layer was washed with water, brine
  7. dry with materialdried over MgSO4
  8. customevaporated in vacuo
  9. customThe crude product was purified by chromatography on silica gel
  10. washElution with Hex

Sources & evidence

ORD record
ord-be5b99aca00c482f98b5bc176d669202
Source dataset
uspto-grants-2008_09
Patent number
US07425631B2

Reaction notes

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