Hydrochloric Acid → HCID 178479215, compound

Participants

Reaction Conditions

Reaction Steps

A solution of N-(cyanoethyl)oxazolidinone 18 (30 g, 0.21 mol) in dry methanol (10.9 g, 0.34 mol) and dry CH2Cl2 (60 mL) was saturated with dry HCl at -15° to 0° C. The mixture was then stirred for 6 h at 0°-20° C. The mixture was evaporated and dried in vacuo for 1 h. The crystalline imidoester hydrochloride was dissolved in dry methanol (120 mL) and cooled to -15° C. To the stirred solution cyclopropylmethylamine (31.2 g, 0.44 mol) was added in drops over a period of 20 min while maintaining the temperature at -15 to 0° C. The mixture was then stirred at -10° C. for 45 min and evaporated. The residue was dissolved in methanol, treated with ether until turbid and was refrigerated for 6 days. The colorless crystalline material was collected and dried to give 59 (28.7 g, 55%), mp 86°-88° C. 1H NMR (DMSO--d6) δ 0.28 (m, 2, --CH--CH2), 0.55 (m, 2, --CH--CH2), 1.05 (m, 1, --CH), 2.68 [t, 2, --CH2 --C(N=)], 3.07 (d, 2, --NH--CH2), 3.54 [t, 2, --CH2 --CH2 --C(N=)], 3.67 (t, 2, --O--CH2 --CH2). 4.30 (t, 2, --OCH2).

Provenance & Evidence