Reacción #69130

Ecuación de reacción

Trans-tert-butyl (R)-1-(4-aminocyclohexyl)ethylcarbamate

D-Lactic Acid

diisopropylethylamine

TBTU

→

title compound

Rendimiento 41.0%

Trans-tert-butyl (R)-1-(4-((R)-2-hydroxypropanamido)cyclohexyl)ethylcarbamate

Rendimiento 41.0%

Disolventes

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe crude mixture was partitioned between ethyl acetate and brine
2. 2
   SecadoThe organic extracts were dried over magnesium sulfate
3. 3
   Filtraciónfiltered
4. 4
   Concentraciónconcentrated in vacuo
5. 5
   OtroThe residue was purified on silica gel by column chromatography (ISCO Companion, 12 g column, 0-10% MeOH/DCM)

Procedimiento

Trans-tert-butyl (R)-1-(4-aminocyclohexyl)ethylcarbamate (125 mg, 0.52 mmol) was dissolved in DMF (3 mL). D-Lactic Acid (49.52 mg, 0.52 mmol), diisopropylethylamine (166.6 mg, 224.5 μL, 1.29 mmol) and TBTU (165.6 mg, 0.5158 mmol) were successively added. The reaction mixture was allowed to stir at ambient temperature for 3 hours. The crude mixture was partitioned between ethyl acetate and brine. The organic extracts were dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified on silica gel by column chromatography (ISCO Companion, 12 g column, 0-10% MeOH/DCM) to afford the title compound (66.1 mg, 41% yield).

Fuente