Triphenylphosphine → HCID 117871161, compound

Participants

Reaction Steps

(2-Hydroxyethyl)-[2-hydroxy-2-(2-isopropyl-pyrimidin-4-yl)-ethyl]-carbamic acid tert-butyl ester (396 mg, 1.22 mmol) was dissolved in methyl-t-butylether (MTBE) (15 ml). Triphenylphosphine (383 mg, 1.46 mmol) was added. To this mixture was added diisopropyl azodicarboxylate (295 mg, 288 μl, 1.46 mmol) dropwise. The solution was stirred at room temperature overnight. A white solid was filtered off, washed with MTBE (2×10 mL). The combined filtrate and washes were concentrated and the resulting residue was purified by Analogix flash column chromatography (40 g silica gel, 0% to 20% ethyl acetate in hexanes gradient) to afford 2-(2-isopropyl-pyrimidin-4-yl)-morpholine-4-carboxylic acid tert-butyl ester (256 mg) as a white solid. (M+H)|=308 m/e. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.35 (d, J=6.82 Hz, 6H) 1.52 (s, 9H) 2.80 (br. s., 1H) 3.06 (d, J=10.61 Hz, 1H) 3.22 (dt, J=13.71, 6.92 Hz, 1H) 3.72 (td, J=11.62, 2.53 Hz, 1H) 3.98 (br. s., 1H) 4.07 (d, J=9.60 Hz, 1H) 4.48 (dd, J=10.48, 2.15 Hz, 2H) 7.31 (d, J=5.05 Hz, 1H) 8.69 (d, J=5.05 Hz, 1H).

Provenance & Evidence