Reacción #69818

Ecuación de reacción

tert-butyl 1-Oxo-2,9-diaza-spiro[5.5]undecane-9-carboxylate

sodium hydride

DMF

1-(chloromethyl)naphthalene

→

title compound

Rendimiento 61.0%

2-(naphthalen-1-ylmethyl)-9-(quinoxalin-2-yl)-2,9-diazaspiro[5.5]undecan-1-one

Rendimiento 61.0%

Disolventes

THF

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGThe mixture was stirred at 45° C. for 18 h
2. 2
   OtroThe reaction mixture was quenched with H2O (50 ml)
3. 3
   Extracciónextracted twice with EtOAc (50 ml)
4. 4
   SecadoThe combined organic layer was dried over Na2SO4
5. 5
   Filtraciónfiltered
6. 6
   Otroevaporated
7. 7
   OtroThe residue was purified by flash chromatography (hexane/EtOAc 2:1)

Procedimiento

A solution of tert-butyl 1-Oxo-2,9-diaza-spiro[5.5]undecane-9-carboxylate (400 mg, 1.5 mmol) in DMF (2 ml) was added slowly at rt to a suspension of sodium hydride 95% (54 mg, 2.24 mmol) in THF (6 ml). The reaction mixture was stirred for 20 min at rt. Then a solution of 1-(chloromethyl)naphthalene (0.33 ml, 2.24 mmol) in THF (2 ml) was added dropwise followed by the addition of tetrabutylammonium iodide (55 mg, 0.15 mmol). The mixture was stirred at 45° C. for 18 h. The reaction mixture was quenched with H2O (50 ml) and extracted twice with EtOAc (50 ml). The combined organic layer was dried over Na2SO4, filtered and evaporated. The residue was purified by flash chromatography (hexane/EtOAc 2:1) to yield 377 mg (61%) of the title compound. [1H NMR (DMSO, 400 MHz) δ 8.01 (m, 1H), 7.93 (m, 1H), 7.85 (m, 1H), 7.55-7.42 (m, 3H), 7.30 (m, 1H), 4.95 (s, 2H), 3.72 (m, 2H), 3.15-2.95 (m, 4H), 1.98-1.82 (m, 2H), 1.78-1.62 (m, 4H), 1.48-1.38 (m, 2H), 1.39 (s, 9H)].

Fuente