Ammonia → HCID 22843776, compound

Participants

Reaction Steps

The ester of Example 6b, (2S-trans)-2-naphthalenyl 3-[2-(8-phenyloctyl)phenyl]oxiranecarboxylate (2.03 g, 4.2 mmol), in methanol (21 mL) was cooled to 5° C. and a solution of ammonia saturated methanol (20 mL) was added dropwise. After stirring for 5 h at 10°-15° C., the solution was evaporated. The residue was dissolved in toluene and evaporated to a solid. The solid was dissolved in toluene and washed with water, NaOH (10%), water, and finally brine. After drying (MgSO4) and evaporation, the residue was dissolved in boiling hexane CH2Cl2 (8:2), filtered and allowed to stand at 20° C. for 4 h. The solid was collected and dried (0.1 mm Hg, 25° C.) to yield the titled oxiranecarboxamide 1.11 g (76%): mp 80°-82° C.; [α]D -8.3° (c 1, CH2Cl2); HPLC RT 5.48 min (2S-enantiomer); 9.99 min (2R-enantiomer) (Bakerbond Chiracel OC; 25 cm×4.6 mm; hexane:isopropanol, 1:1; 1.0 mL/min; UV detection at 211 nm); HPLC showed the product at >99% e.e. Anal. Calcd for C23H29O2N: C, 78.59; H, 8.32; N, 3.99. Found: C, 78.35; H, 8.34; N, 3.90.

Provenance & Evidence