Acetic Acid → HCID 10505413, compound

Participants

Reaction Steps

Glacial acetic acid (0.8 mL), benzylamine (1.6 mL, 15 mmol), and sodium cyanoborohydride (0.9 g, 14 mmol) were added under an argon atmosphere to a solution of 17-keto derivative (18) (2 g, 5 mmol) in anhydrous 1,2-dichloroethane (30 mL). The resulting mixture was stirred at room temperature for 72 h. Additional amounts of anhydrous benzylamine (0.4 mL), acetic acid (0.2 mL), and sodium cyanoborohydride (0.25 g) were added to the mixture, and stirring was continued for 24 h. The solvent was removed under reduced pressure, the residue was diluted with water (50 mL), and extracted with ethyl acetate (3×150 mL). The combined organic layer was washed with water (100 mL), sodium bicarbonate solution (100 mL), brine (100 mL), and dried over anhydrous sodium suleate. The organic layer on evaporation under reduced pressure gave crude product (3.1 g) which was subjected to column chromatography on silica gel using hexane, followed by hexane-CH2Cl2 (1:1), and finally CH2Cl2. Appropriate fractions were combined and evaporated under reduced pressure to give pure amine derivative (19) (2.2 G, 89%). The mp for aminederivative (19) could not be determined as it was a sticky solid which was used without any further purification: IR (KBr) 2921, 1608, 1508, 1453, 1264, 1209, 1119, 1019, 729 cm-1 ; 1H NMR (CDCl3) δ 7.52-7.25 (m, 11 H), 6.85 (s, 1 H), 6.65 (s, 1 H), 4.20 (q, J=8.5 Hz, J=8.5 Hz, 2 H), 3.80 (s, 2 H) 2.75 (m, 1 H) 2.65 (t, J=8.5 Hz, 1 H), 2.35-2.12 (m, 4 H), 2.10 (s, 2 H), 1.85 (m, 4 H), 1.75-1.52 (m, 6 H), 1.40 (t, J=8.5, 3 H), 0.78 (s, 3 H).

Provenance & Evidence