Hydrochloric Acid → HCID 70204637, compound

Participants

Reaction Steps

5-Methylthieno[3,2-b]pyridine (285 mg, 1.91 mmol, prepared according to Gronowitz et al., Acta Chemica Scandinavica B, 29:233-238 (1975)), diisopropylamine (270 uL, 1.91 mmol) and nBuLi (2.5 M in hexanes, 765 uL, 1.91 mmol) were combined in THF (8 mL). After 20 minutes of stirring, 1,2,3,5,6,7-hexahydro-pyrrolizinium perchlorate from Example 15a (200 mg, 0.95 mmol) was added. The mixture was allowed to warm to ambient temperature and 2 N aqueous HCl was added. The reaction mixture was washed with Et2O and the aqueous phase was basified with 15% NaOH solution and extracted with CH2Cl2 (3×). The organic phases were combined, dried (MgSO4), concentrated and chromatographed (silica gel; CHCl3 /MeOH, 99:1) to afford a solid (79 mg, 32%): 1H NMR (CDCl3, 300 MHz) δ 1.80-1.94 (m, 4H), 1.98-2.07 (m, 2H), 2.16-2.24 (m, 2H), 2.64 (s, 3H), 2.64-2.71 (m, 2H), 3.22-3.28 (m, 2H), 7.02 (d, J=8 Hz, 1H), 7.16 (s, 1H), 7.92 (d, J=8 Hz, 1H); MS (CI/NH3) m/z: 259 (M+H)+.

Provenance & Evidence