Reacción #2446081

Ecuación de reacción

1-((tert-butoxycarbonyl)(cyclohexyl)amino)propan-2-yl 2,4,6-trimethyl-benzoate

formaldehyde

sodium triacetoxyborohydride

acetic acid

→

1-(cyclohexyl(methyl)amino)propan-2-yl-2,4,6-trimethylbenzoate

Disolventes

DCM

dioxane-HCl

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroSolvent was evaporated
2. 2
   workup.DISSOLUTIONCrude solid was dissolved in DCE (10 ml)
3. 3
   OtroThe resultant reaction mixture
4. 4
   workup.STIRRINGwas stirred at rt for 16 hours
5. 5
   Lavadowashed with 1N NaOH, water and brine
6. 6
   SecadoThe organic layer was dried over sodium sulphate
7. 7
   Concentraciónconcentrated to dryness
8. 8
   OtroThe crude compound was purified by column chromatography

Procedimiento

1-((tert-butoxycarbonyl)(cyclohexyl)amino)propan-2-yl 2,4,6-trimethyl-benzoate (1.0 g, 2.48 mmol) was dissolved in dioxane-HCl (15 mL). The reaction mixture was stirred at rt for 2 hours. Solvent was evaporated. Crude solid was dissolved in DCE (10 ml) and formaldehyde (0.34 mL, 3.96 mmol), and sodium triacetoxyborohydride (1.67 g, 7.92 mmol) and acetic acid (0.5 mL) were added at 0° C. The resultant reaction mixture was stirred at rt for 16 hours. The reaction mixture was diluted in DCM and washed with 1N NaOH, water and brine. The organic layer was dried over sodium sulphate and concentrated to dryness. The crude compound was purified by column chromatography to obtain 1-(cyclohexyl(methyl)amino)propan-2-yl-2,4,6-trimethylbenzoate. Yield: 0.6 (76%); 1H NMR (400 MHz, CDCl3) δ 6.82 (s, 2 H), 5.27-5.25 (m, 1 H), 2.64-2.62 (m, 1 H), 2.51-2.46 (m, 1 H), 2.29 (s, 9 H), 2.25 (s, 3 H), 1.75-1.74 (m, 4 H), 1.33-1.31 (d, J=6 Hz, 3 H), 1.18-1.13 (m, 4 H), 1.09-1.03 (m, 1H); LCMS: m/z=317.8 [M+H], RT=2.98 min (Column: X, Program: P1).

Fuente