Pyrrolidine → HCID 67246961, compound

Participants

Reaction Steps

To a solution of toluene-4-sulfonic acid 2-fluoro-5-nitro-benzyl ester (compound of step B of example 29) (0.696 g, 2.31 mmoles) in 1,4-dioxane (20 mL) was added TEA (0.32 mL, 2.31 mmoles) and pyrrolidine (0.19 mL, 2.31 mmoles). The reaction mixture was stirred for 24 h at room temperature, concentrated and purified by TLC (petroleum ether/AcOEt/NH4OH//8/2/0.2). The expected compound was obtained as a yellow oil (0.399 g, 77% yield). MALDI-TOF: m/z 225.1 [M+H]+. 1H NMR (300 MHz, CDCl3) δ8.38; (dd, J=6.2 Hz and 2.9 Hz, 1H), 8.15; (ddd, 4-CH, J=8.9 Hz, 2.9 Hz and 4.4 Hz, 1H), 7.17; (dd, J=8.9 Hz and 8.9 Hz, 1H), 3.76; (s, 2H), 2.5-2.6; (m, 4H), 1.8-1.9; (m, 4H). 13C NMR (75 MHz, CDCl3) δ127.0; (CH, d, J=6.4 Hz), 124.5; (CH, d, J=10.1 Hz), 116.2; (CH, d, J=24.9 Hz), 54.1; (CH2), 52.2; (CH2), 23.5; (CH2).

Provenance & Evidence