Diethyl cyanophosphonate → HCID 68925513, compound

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence