تفاعل #44859

معادلة التفاعل

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

المردود 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

المردود 92.1%

المذيبات

THF

ظروف التفاعل

المعالجة

1. 1
   تركيزThe mixture was concentrated
2. 2
   أخرىto remove the solvent
3. 3
   workup.ADDITIONthe residue was poured into sat. NaHCO3 aq. The mixture
4. 4
   استخلاصwas extracted with CH2Cl2 for three times
5. 5
   تجفيفthe organic layer was dried over Na2SO4
6. 6
   أخرىRemoval of the solvent
7. 7
   أخرىgave a residue, which
8. 8
   أخرىwas chromatographed on a column of silica gel
9. 9
   غسيلeluting MeOH/CH2Cl2 (1:10)

الإجراء التجريبي

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.

المصدر