1,2-Dichloroethane → tert-butyl (R)-1-((3S,4S)-4-(4-chlorophenyl)-3,4-dihydroxy-3-methylpiperidin-1-yl)-3-methyl-1-oxobutan-2-ylcarbamate

Participants

Reaction Steps

To a mixture of (3S,4S)-4-(4-chlorophenyl)-3-methylpiperidine-3,4-diol (91 g, 376 mmol), Boc-D-Valine (83.1 g, 382 mmol), HOBt (69.2 g, 452 mmol), EDC (87 g, 452 mmol) in CH2Cl2 (800 mL) and DMF (80 mL) was added DIPEA (132 mL, 753 mmol) at room temperature. The mixture was stirred at room temperature overnight. The reaction was concentrated and the residue partitioned between EtOAc and water. The EtOAc layer was washed with 1N HCl, sat. aq. NaHCO3, and brine to give the crude product (180 g, ˜80% purity) which was used directly in the next transformation.

Provenance & Evidence