Potassium Sodium Tartrate → HCID 18507140, compound

Participants

Reaction Steps

To a solution of 2-(5-bromo-pyridin-2-yl)-5-chloro-2-(3-methoxy-phenyl)-pentanenitrile (0.54 g, 1.43 mmol) in CH2Cl2 (3 mL) at −78° C. was added DIBAL in CH2Cl2 (1M, 3.2 mL). The reaction mixture was stirred at −78 for 1 h and at room temperature for 4 h. The solution was poured to a saturated aqueous solution of Rochelle's salt (10 mL) and the resulting mixture was stirred vigorously for 16 h. The aqueous layer was washed with CH2Cl2 (3×10 mL), and the combined extracts were dried over Na2SO4 and concentrated. Purification by flash chromatography with CH2Cl2/MeOH (10:1) yielded 0.36 g of 5-bromo-3′-(3-methoxy-phenyl)-1′,2′,3′,4′,5′,6′-hexahydro-[2,3′]bipyridinyl. 1HNMR (400 MHz, CDCl3) δ 8.62 (s, 1H), 7.63 (dd, 1H), 7.24-7.18(m, 1 H), 6.91 (d, 1H) 6.81-6.67 (comp, 3H), 3.96-3.90 (m, 1H), 3.75 (s, 3H), 3.09-3.00 (comp, 2H), 2.82-2.74 (m, 1H), 2.54-2.48 (m, 1H), 2.41-2.34 (m, 1H), 1.64-1.60 (m, 1H), 1.38-1.31 (m, 1H); MS (M+1) 347.1, 349.1.

Provenance & Evidence