Diisopropylethylamine → HCID 58694585, compound

Participants

Reaction Steps

A solution of 89.0 mg (0.231 mmol) 4-[4-amino-3-(4,4-dimethyl-cyclohex-1-enyl)-phenyl]-piperidine-1-carboxylic acid tert-butyl ester (as prepared in the previous step) in 10 mL CH2Cl2 was treated with 77.8 mg (0.255 mmol) 4-cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylate potassium salt (as prepared in Example 1, step (d)), 162 mg (0.347 mmol) PyBrOP, and 121 μL (0.694 mmol) DIEA and stirred at RT for 2 h. The mixture was diluted with CH2Cl2 (20 mL) and washed with saturated NaHCO3 (1×15 mL) and water (1×15 mL). The organic layer was dried (MgSO4) and concentrated in vacuo. Silica gel chromatography of the residue on a Varian MegaBond Elut 50-gm column with 10-25% EtOAc-hexane afforded 124 mg (84%) of the title compound as an off-white solid: Mass spectrum (ESI, m/z): Calcd. for C31H44N5O4Si, 578.3 (M−C4H9+2H), found 578.0.

Provenance & Evidence