Stannous Chloride → HCID 57886759, compound

Participants

Reaction Steps

To a solution of 1-(2-fluoro-5-nitro-benzyl)-pyrrolidine (420 mg, 1.87 mmol) in THF (20 mL) was added a solution of SnCl2 (1421 mg, 7.49 mmol) in THF (5 mL) and HCl 1M (2.1 mL). The reaction mixture was refluxed for 4 h and concentrated. Saturated solution of NaHCO3 was added until pH8. Aqueous layer was extracted with CH2Cl2 (5×50 mL). The organic layer was dried over MgSO4, filtered, evaporated. Expected compound was precipited with MeOH and purified by TLC (DCM/MeOH/NH4OH//9.5/0.5/0.35) and obtained as a yellow oil (229.5 mg, 63% yield). MALDI-TOF: m/z 195.2 [M+H]+. 1H NMR (300 MHz, CDCl3) δ6.76; (dd, J=9.5 Hz and 8.7 Hz, 1H), 6.69; (dd, J=6.1 Hz and 2.9 Hz, 1H), 6.46; (ddd, J=8.7 Hz, 4.1 Hz and 2.9 Hz, 1H), 3.57; (d, J=1.6 Hz, 2H), 3.3-3.5; (s large, 2H), 2.5-2.6; (m, 2H), 1.7-1.8; (m, 4H). 13C NMR (75 MHz, CDCl3) δ117.5; (CH, d, J=3.5 Hz), 115.7; (CH, d, J=23.6 Hz), 115.0; (CH, d, J=7.7 Hz), 54.1; (CH2), 52.8; (CH2), 23.6; (CH2).

Provenance & Evidence