Trifluoroacetic acid → HCID 68089352, compound

Participants

Reaction Steps

A mixture of 2 g (4.99 mmol) rac-[(3S,4R)-1-Benzyl-4-(4-chloro-phenyl)-4-methyl-pyrrolidin-3-yl]-carbamic acid tert-butyl ester, 0.67 g (5.99 mmol) potassium tert.-butoxide and 0.786 (6.24 mmol) dimethyl sulfate in 40 mL DMSO was stirred for 1 h at room temperature. The mixture was poured on ice-water containing NaOH (1N) and extracted with TBME. The combined organic layers were washed with brine, dried with Na2SO4, filtered and evaporated. The residue was dissolved in 30 mL DCM, 5.69 g (49.9 mmol) TFA was added and the mixture was stirred at room temperature for 15 h. Ice-water was added and the pH was adjusted to 12 with NaOH aq. and stirred for 15 min The organic layer was separated and washed with brine and the aqueous layer was extracted with DCM. The combined organic layers were dried with Na2SO4, filtered and evaporated. The residue was taken up on isolute and subjected to purification by chromatography on silica eluting with a gradient formed from DCM, methanol and NEt3 to yield after evaporation of the product containing fractions 0.83 g (53%) of the title compound as light yellow oil. MS m/e: 315.1 [M+H]+.

Provenance & Evidence