1,2-Dichloroethane → (3,4-Difluorophenyl)(phenyl)methyl quinuclidine-3-carboxylate

Quinuclidine-3-carboxylic acid hydrochloride (80 mg, 0.42 mmol), EDC (120 mg, 0.62 mmol), and HOBT (96 mg, 0.62 mmol) were dissolved in dry THF (3 ml). (3,4-Difluorophenyl)(phenyl)methanol (101 mg, 0.46 mmol) was dissolved in dry THF (2 ml) and then added to the reaction mixture. Triethylamine (203 μl, 1.46 mmol) was finally added, and the resulting reaction was stirred at room temperature overnight. The volatiles were evaporated, and the crude was taken up with EtOAc and washed with water and then with sat. NaHCO3. The organic phase was dried over sodium sulfate, filtered, and evaporated under vacuum. The crude was purified by flash chromatography (DCM/MeOH=9/1) to obtain (3,4-difluorophenyl)(phenyl)-methyl quinuclidine-3-carboxylate (65 mg, mixture of diastereoisomers).

1. additionadded to the reaction mixture
2. customthe resulting reaction
3. customThe volatiles were evaporated
4. washwashed with water
5. dry with materialThe organic phase was dried over sodium sulfate
6. filtrationfiltered
7. customevaporated under vacuum
8. customThe crude was purified by flash chromatography (DCM/MeOH=9/1)

ORD record

ord-c0f7c0dcb0224b5ca311e8403c7d6e60

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08604015B2