Phosphorus oxychloride → HCID 86583778, compound

Participants

Reaction Conditions

Reaction Steps

(175 mg, 0.54 mmol) of (2) was dissolved in 4 ml of pyridine and the mixture was cooled to 0° C. Phosphorus oxychloride (0.2 ml, 2.15 mmol) was added dropwise and after 10 minutes of stirring the reaction mixture was poured into 20 ml of ice water and the organic material was extracted into 5×10 ml of ethyl acetate. The combined organic extract was washed with 2×20 ml of water, 1×20 ml of brine and dried over magnesium sulphate. The solvent was evaporated to afford 140 mg of (S,S) [1-(2-Cyano-2,5-dihydro-pyrrole-1-carbonyl)-2,2-dimethyl-propyl]-carbamic acid tert-butyl ester (3). Oil, 85% yield. 1H-NMR (CDCl3, 200 MHz) δ: 1.05 (s, 9H); 1.42 (s, 9H); 4.22 (d, 1H); 4.39-4.53 (m, 1H); 4.65-4.77 (m, 1H); 5.30 (d, 1H); 5.41-5.48 (m, 1H); 5.83-5.90 (m, 1H); 6.09-6.15 (m, 1H).

Provenance & Evidence