Potassium Carbonate → HCID 86653083, compound

Participants

Reaction Steps

To a solution of crude tert-butyl (R)-3-hydroxy-1-(methylamino)propan-2-ylcarbamate in acetone (30 mL) and water (10 mL), there was added K2CO3 (12.8 g, 92.4 mmol), followed by Teoc-OSu (8.0 g, 30.8 mmol). The resulting mixture was stirred at rt until no starting material remained (˜1 h). Acetone was removed under vacuum and the aqueous residue was extracted with CH2Cl2 (4×15 mL). The combined organic layers were concentrated and the crude residue was purified by flash column chromatography to give (2R)-2-(t-butoxycarbonylamino)-3-(N-methyl-N-(2-(trimethylsilyl)ethoxycarbonyl)amino)propan-1-ol (2.12 g, 20% steps). 1H NMR (400 MHz, CDCl3): 5.08 (br, 1 H), 4.14 (m, 2 H), 3.66-3.42 (m, 4 H), 3.02 (m, 1 H), 2.90 (s, 3 H), 1.40 (S, 9 H), 0.98 (m, 2 H), 0.02 (s, 9 H); MS m/z 349 (M+H+).

Provenance & Evidence