2-Aminocyclohexanol → benzyl N-(2-hydroxycyclohexyl)carbamate

Participants

Reaction Steps

To a solution of benzyl 2,5-dioxocyclopentanecarboxylate (2.58 g, 10.35 mmol) in MeOH (20 mL) at 0° C. was added 2-aminocyclohexanol (1.25 g, 10.87 mmol). The reaction mixture was stirred at room temperature for 18 hr and quenched by addition of 0.25 N HCl (8 mL). MeOH was removed in vacuo and the aqueous layer was extracted with CH2Cl2 (4×10 mL). The combined organic portions were washed with saturated NaCl (20 mL), dried over Na2SO4, filtered and concentrated under reduced pressure. The resulted brown oil was purified by ISCO chromatography (40 g column) using hexanes/EtOAc (0-5% over 15 min, 5-10% over 7 min) to give benzyl 2-hydroxycyclohexylcarbamate as a light yellow solid at a retention time of 11-13 min (2.15 g, 83% yield) HPLC: RT=2.83 min, Purity 95% (HPLC Method 1) NMR: 400 MHz 1H (CDCl3) 7.33 ppm, 5 H, m; 5.16 ppm, 1 H, m; 5.09 ppm, 2 H, s; 3.95 ppm, 1 H s; 3.68 ppm, 1 H m; 1.54 ppm, 8 H, m.

Provenance & Evidence