Trichloroacetimidic acid (S)-1-[3,5-bis(trifluoromethyl)phenyl]ethyl ester → HCID 86610907, compound

Participants

Reaction Steps

The title compound was prepared from (3R,4S) tert-butyl-3-hydroxy-4-(4-fluorophenyl)pyrrolidine-1-carboxylate (Step B, Rt 13.686 min) and (1S)-1-[3,5-bis(trifluoromethyl)phenyl]ethyl-2,2,2-trichloroethanimidoate (Example 1, step C) according to the procedure for Example 1, Step D. The product mixture was further purified by preparative HPLC on ChiralPak OD column eluting with heptanes/ethanol (98/2) to obtain the faster moving minor isomer (epimeric at the benzylic methyl position) and slower moving title compound. 1H-NMR (CDCl3): (rotamers): δ: 1.43-47 (2d, 3H, 6.5 Hz), 1.49-1.52 (2s, 9H), 3.3-3.5 (m, 3H), 3.75-3.95 (m, 3H), 4.53 (q, 1H, 6.5 Hz), 6.95 (t, 2H), 7.05 (m, 2H), 7.53 (s, 2H), 7.76 (s, 1H)ppm. MS: 466 (M-t-Bu)+ observed.

Provenance & Evidence