Pyridine → HCID 59201347, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of crude tert-butyl (2R,3S)-2-amino-3-cyclohexyl-3-hydroxypropyl(methyl)carbamate (300 mg, 1.05 mmol) in anhydrous THF was added pyridine (846 μL, 10.50 mmol) and TMSCl (663 μL, 5.25 mmol). The mixture was heated to 60° C. and maintained for 20 min, then quenched with satd aq NaHCO3 (5 mL) and extracted with EtOAc (2×20 mL). The combined organic layers were washed with brine, dried over NaSO4 and concentrated to afford tert-butyl (2R,3S)-2-amino-3-cyclohexyl-3-(trimethylsilyloxy)propyl(methyl)carbamate (350 mg, yield 93.1%). 1H NMR (400 MHz, MeOD): 0.13 (s, 9H), 0.80-1.40 (m, 6H), 1.40 (s, 9H), 1.50-2.10 (m, 5H), 2.90 (s, 3H), 3.15-3.50 (m, 4H). MS (E/Z): 359.0 (M+H+).

Provenance & Evidence