Ammonium Chloride → (S)-4-[2-(3-fluoro-2-methyl-benzyl)-1-phenyl-indolizine-3-carbonyl]-2-(2-hydroxy-ethyl)-piperazine-1-carboxylic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

A 1 M solution of tetrabutylammonium fluoride in THF (2.82 ml, 2.82 mmol) was added to a solution of the compound of step 4 (1.29 g, 1.88 mmol) in 7.5 ml of THF cooled to 0° C. under argon. The mixture was stirred at room temperature for 2 h and then 100 ml of a saturated solution of ammonium chloride were added. The solution was extracted twice with 50 ml each of EA, and the combined organic phases were washed with brine, dried over sodium sulfate, filtered and evaporated to dryness under reduced pressure. The residue was purified by chromatography on silica gel (DCM/MOH, 100:0, then 98:2) to give 1.069 g of the title compound as an off-white powder melting at 85° C.

Provenance & Evidence