1,2-Dichloroethane → HCID 57889753, compound

Participants

Reaction Steps

N-Boc-D-valine (2.22 g, 10.2 mmol), EDC (1.96 g, 10.2 mmol), HOBt (1.38 g, 10.2 mmol) was dissolved in dichloromethane (40 mL). DIPEA (4.0 mL, 23.3 mmol) and 4-hydroxy-(4-chlorophenyl)piperidine (1.98 g, 9.34 mmol) was added and the solution was stirred at rt for 2 h. The reaction was concentrated and the resulting oily residue partitioned between EtOAc (150 mL) and water (50 mL), shaken and then separated. The organic layer was then washed with aq NaHCO3 (50 mL) and brine and the combined organic fractions were dried over solid sodium sulfate. The solution was filtered and concentrated by to give (R)-tert-butyl 1-(4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl)-3-methyl-1-oxobutan-2-ylcarbamate (3.9 g) as a white foam. MS found: (M+)+=411.1.

Provenance & Evidence