反応 #44859

反応方程式

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

収率 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

収率 92.1%

溶媒

THF

反応条件

後処理

1. 1
   濃縮The mixture was concentrated
2. 2
   その他to remove the solvent
3. 3
   workup.ADDITIONthe residue was poured into sat. NaHCO3 aq. The mixture
4. 4
   抽出was extracted with CH2Cl2 for three times
5. 5
   乾燥the organic layer was dried over Na2SO4
6. 6
   その他Removal of the solvent
7. 7
   その他gave a residue, which
8. 8
   その他was chromatographed on a column of silica gel
9. 9
   洗浄eluting MeOH/CH2Cl2 (1:10)

実験手順

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.

出典