反応 #49171

反応方程式

pyridine

compound 3a

[6-(4-Hydroxy-2-hydroxymethyl-pyrrolidin-1-yl)-6-oxo-hexyl]-carbamic acid benzyl ester

dimethylamino pyridine

DMT-Cl

pyridine

→

crude product

(6-{2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-pyrrolidin-1-yl}-6-oxo-hexyl)-carbamic acid benzyl ester

反応条件

後処理

1. 1
   その他The excess DMT-Cl was quenched by the addition of methanol (25 mL)
2. 2
   その他The solution was dried under reduced pressure
3. 3
   洗浄washed with saturated bicarbonate solution, brine and water
4. 4
   乾燥The organic layer was dried over anhydrous sodium sulfate
5. 5
   ろ過filtered
6. 6
   その他evaporated

実験手順

Referring to scheme 1, compound 3a (14 g, 38.4 mmol) was co-evaporated with anhydrous pyridine three times and then dissolved in pyridine (60 mL). To this solution dimethylamino pyridine (0.488 g, 4 mmol) and DMT-Cl (13.6 g, 40.3 mmol, 1.05 equiv.) were added at room temperature. The reaction mixture was stirred at room temperature for 16 h. The excess DMT-Cl was quenched by the addition of methanol (25 mL). The solution was dried under reduced pressure. To the residue was suspended in ethyl acetate (300 mL) and washed with saturated bicarbonate solution, brine and water. The organic layer was dried over anhydrous sodium sulfate, filtered and evaporated. 24.2 g of the crude product was obtained after removal of the solvent. Upon purification over silica gel using 2% MeOH/DCM compound 4a (21.3 g, 83%) was obtained as white foamy solid.

出典