Reacción #164152

Ecuación de reacción

2-phenyl-2-(phenylamino)acetic acid

EDC

HOBt

8-methyl-8-azabicyclo[3.2.1]octan-3-ol

→

title compound

Rendimiento 7.0%

8-methyl-8-azabicyclo[3.2.1]octan-3-yl 2-phenyl-2-(phenylamino)acetate

Rendimiento 7.0%

Disolventes

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   ConcentraciónThe reaction is concentrated under reduced pressure
2. 2
   SecadoThe organic phase is dried over Na2SO4
3. 3
   Filtraciónfiltered
4. 4
   Otroevaporated to dryness
5. 5
   OtroThe resulting crude is purified by preparative HPLC
6. 6
   OtroThe collected compound is partitioned between 1N NaHCO3 and DCM
7. 7
   Otrothe organic phase is separated
8. 8
   Secadodried over Na2SO4
9. 9
   Filtraciónfiltered
10. 10
    Otroevaporated under vacuum

Procedimiento

A mixture of 2-phenyl-2-(phenylamino)acetic acid I1 (250 mg, 0.90 mmol), EDC (255 mg, 1.35 mmol), HOBt (245 mg, 1.80 mmol) and 8-methyl-8-azabicyclo[3.2.1]octan-3-ol (380 mg, 2.71 mmol) in dry DMF (10 mL) is heated under microwave irradiation at 100° C. for 1 hour (LC-MS monitoring: complete conversion). The reaction is concentrated under reduced pressure and the residue is portioned between EtOAc and water. The organic phase is dried over Na2SO4, filtered and evaporated to dryness. The resulting crude is purified by preparative HPLC. The collected compound is partitioned between 1N NaHCO3 and DCM, the organic phase is separated dried over Na2SO4, filtered and evaporated under vacuum to give 20.1 mg of the title compound as a colorless oil (7% yield, mixture of diastereoisomers).

Fuente