Trifluoroacetic acid → 3,4-Dichlorobenzaldehyde

Trifluoroacetic acid (0.3 mL) was added at room temperature to a solution of 3-benzyl-3-(3,4-dichloro-benzoyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (40 mg, 0.092 mmol) in DCM (3 mL). The reaction mixture was stirred at room temperature for 1 hour, then poured into aqueous NaOH (1.0 M), diluted with water and extracted with DCM. The combined organic extracts were dried over MgSO4, filtered and evaporated under reduced pressure. The residue was purified by flash chromatography (3% to 10% of MeOH in DCM+0.5% of NH4OH) to give 15 mg (48% yield) of 3-benzyl-pyrrolidin-3-yl)-(3,4-dichloro-phenyl)-methanone as a yellow oil. This material was dissolved in DCM and a solution of HCl (1.0 M in Et20, 1.1 equivalents) was added, the resulting mixture was concentrated under reduced pressure and the residue was triturated with Et2O to give 17 mg of 3-benzyl-pyrrolidin-3-yl)-(3,4-dichloro-phenyl)-methanone hydrochloride as a white solid; MS=334 [M+H]+.

1. extractionextracted with DCM
2. dry with materialThe combined organic extracts were dried over MgSO4
3. filtrationfiltered
4. customevaporated under reduced pressure
5. customThe residue was purified by flash chromatography (3% to 10% of MeOH in DCM+0.5% of NH4OH)

ORD record

ord-dd0d22668b1b4417ab3648d335d1c159

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08513425B2