Sodium Sulfate → HCID 178491122, compound

Participants

Reaction Steps

A suspension of tert-butyl (trans)-4-aminocyclohexylcarbamate (1.0 g, 4.67 mmol) in dichloromethane (30 mL) was treated with 4-methoxybenzaldehyde (0.568 mL, 4.67 mmol) and magnesium perchlorate (0.052 g, 0.233 mmol) and stirred at room temperature overnight. A large excess of solid Na2SO4 was added, and the reaction mixture was stirred for 1 h., filtered, and the filter cake was rinsed with MeOH. The filtrate and rinse were combined and concentrated to yield a white solid, which was dissolved in MeOH (10 mL). This solution was treated with NaBH4 (0.265 g, 7.00 mmol) in a single portion. The reaction mixture became a light yellow solution which was stirred at room temperature for 1.5 h. The reaction was quenched with 1.0N NaOH, diluted with water (150 mL), and stirred for 30 min. The resulting white solid was collected by filtration, washed with water, and air dried to provide 15A (1.26 g, 81% yield). MS (ES): m/z=335 [M+H]+. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.20 (d, 2H, J=8.5 Hz); 6.83 (d, 2H, J=8.5 Hz); 6.63 (d, 1H, J=8.0 Hz); 3.70 (s, 2H); 3.60 (br. s, 1H); 3.31 (s, 3H); 3.08-3.18 (m, 1H); 2.06-2.25 (m, 1H); 1.65-1.88 (m, 4H); 1.34 (s, 9H); 0.93-1.12 (m, 4H).

Provenance & Evidence