1-Boc-3-aminopyrrolidine → HCID 57461720, compound

Participants

Reaction Steps

tert-Butyl 3-[5-acetyl-4-(4-fluorophenyl)-1H-imidazol-1-yl]pyrrolidine-1-carboxylate [C16, prepared according to the general procedure for the synthesis of tert-butyl 3-[5-acetyl-4-(4-fluorophenyl)-1H-imidazol-1-yl]azetidine-1-carboxylate (C3) in Example 1, except that tert-butyl 3-aminopyrrolidine-1-carboxylate was used in place of tert-butyl 3-aminoazetidine-1-carboxylate; NMR (400 MHz, CDCl3) δ 1.49 (s, 9H), 2.13 (s, 3H), 2.22 (m, 1H), 2.45 (m, 1H), 3.47-3.88 (m, 4H), 5.55 (m, 1H), 7.15 (dd, J=8.7, 8.7 Hz, 2H), 7.46 (dd, J=8.7, 5.4 Hz, 2H), 7.69 (br s, 1H)] was subjected to reaction conditions similar to those used for preparation of tert-butyl 3-[5-(2-aminopyrimidin-4-yl)-4-(4-fluorophenyl)-1H-imidazol-1-yl]azetidine-1-carboxylate (C4) in Example 1, to provide the product as a solid. Yield: 6.1 g, 14.4 mmol, 67%. 1H NMR (400 MHz, CD3OD) δ 1.48 (s, 9H), 2.32-2.50 (m, 2H), 3.48-3.65 (m, 3H), 3.81 (m, 1H), 5.42 (m, 1H), 6.42 (d, J=4.9 Hz, 1H), 7.09 (dd, J=8.7, 8.7 Hz, 2H), 7.43 (dd, J=8.5, 5.3 Hz, 2H), 7.92 (s, 1H), 8.13 (d, J=4.5 Hz, 1H).

Provenance & Evidence