反应详情

Quinuclidine-3-carboxylic acid hydrochloride (150 mg, 0.78 mmol), EDC (225 mg, 1.17 mmol) and HOBT (180 mg, 1.17 mmol) were dissolved in dry THF (7.5 ml). Bis(4-chlorophenyl)methanol (218 mg, 0.86 mmol) was added followed by TEA (382 μl, 2.74 mmol). The resulting reaction was stirred at room temperature overnight. THF was removed under vacuum, and the crude was partitioned between EtOAc and water. The organic phase was washed with sat. NaHCO3, dried over sodium sulphate, filtered, and evaporated to dryness. The crude was purified by flash chromatography (EtOAc/MeOH=8/2 to 7:3+1% of NH4OH) to obtain bis(4-chlorophenyl)methyl quinuclidine-3-carboxylate (85.0 mg, racemic mixture).

1. customThe resulting reaction
2. customTHF was removed under vacuum
3. customthe crude was partitioned between EtOAc and water
4. washThe organic phase was washed with sat. NaHCO3
5. dry with materialdried over sodium sulphate
6. filtrationfiltered
7. customevaporated to dryness
8. customThe crude was purified by flash chromatography (EtOAc/MeOH=8/2 to 7:3+1% of NH4OH)