Diisopropylethylamine → HCID 59444213, compound

Participants

Reaction Steps

To a solution of 2-(4-(tert-butoxycarbonylamino)tetrahydro-2H-pyran-4-yl)acetic acid (step 2, 0.125 g, 0.48 mmol) in anhydrous DMF (1 mL) was sequentially added (S)-4-(4-chlorophenyl)-3,3-dimethylpiperidin-4-ol (0.182 g, 0.48 mmol), diisopropylethylamine (0.17 mL, 0.96 mmol) and (benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (0.225 g, 0.50 mmol) at room temperature. Upon completion of addition, the reaction mixture was stirred at room temperature for 20 h and then partitioned between ethyl acetate (20 mL) and 1N HCl (10 mL). The ethyl acetate layer was separated, washed sequentially with 1N NaOH (10 mL), brine (10 mL), dried over sodium sulfate and concentrated to yield a residue. The residue was purified using a pre-packed silica gel column (40 g) employing hexane and ethyl acetate. The desired fractions were collected and concentrated under reduced pressure to yield the title compound (0.175 g) as a foamy solid. MS (ESI+)=481.1 (M+H)+.

Provenance & Evidence