Reacción #44859

Ecuación de reacción

tert-butyl 4-{[4-({[(3-isopropyl-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)carbonyl]amino}methyl)piperidin-1-yl]methyl}tetrahydro-2H-pyran-4-carboxylate

HCl

→

title compound

Rendimiento 92.1%

4-{[4-({[(3-isopropyl-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)carbonyl]amino}methyl)piperidin-1-yl]methyl}tetrahydro-2H-pyran-4-carboxylic acid

Rendimiento 92.1%

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   ConcentraciónThe mixture was concentrated
2. 2
   Otroto remove the solvent
3. 3
   workup.ADDITIONthe residue was poured into sat. NaHCO3 aq. The mixture
4. 4
   Extracciónwas extracted with CH2Cl2 for three times
5. 5
   Secadothe organic layer was dried over Na2SO4
6. 6
   OtroRemoval of the solvent
7. 7
   Otrogave a residue, which
8. 8
   Otrowas chromatographed on a column of silica gel
9. 9
   Lavadoeluting MeOH/CH2Cl2 (1:10)

Procedimiento

To a stirred solution of tert-butyl 4-{[4-({[(3-isopropyl-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)carbonyl]amino}methyl)piperidin-1-yl]methyl}tetrahydro-2H-pyran-4-carboxylate (3.67 g, 7.13 mmol, step 6) in THF (80 mL) was added conc. HCl (40 mL) at 0° C. and the resulting mixture was stirred for 20 h at room temperature. The mixture was concentrated to remove the solvent and the residue was poured into sat. NaHCO3 aq. The mixture was extracted with CH2Cl2 for three times and the organic layer was dried over Na2SO4. Removal of the solvent gave a residue, which was chromatographed on a column of silica gel eluting MeOH/CH2Cl2 (1:10) to give 3.01 g (92%) of the title compound. The product was recrystalized from THF to give the titled compound (0.893 g) as white crystals.

Fuente