Morpholine → tert-Butyl4-(3-{2-[3-(4-morpholinylmethyl)phenoxy]ethoxy}-2-pyrazinyl)-1-piperazinecarboxylate

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Reaction Steps

A stirred solution of the aldehyde from step 3 above (71.2 mg, 0.166 mmol) in 1,2-dichloroethane (5 mL) was treated with morpholine (19 mg, 0.22 mmol), 3 Å molecular sieves and sodium triacetoxyborohydride (52 mg, 0.25 mmol). The mixture was stirred at room temperature for 5 h (TLC monitoring). The solution was filtered and the filtrate was treated with an excess of saturated aqueous sodium bicarbonate. The ether extracts were separated and dried over magnesium sulfate. The mixture was filtered and solvent was removed in vacuo to give 54 mg (65%) of the title product as a yellow oil. Pure by NMR. 1H NMR (CDCl3) δ 1.4 (s, 9H); 2.35 (m, 4H); 3.4 (m, 10H); 3.65 (m, 4H); 4.3 (m, 2H); 4.65 (m, 2H); 6.75 (d, 1H); 6.9 (m, 2H); 7.2 (t, 1H); 7.5 (s, 1H); 7.7 (s, 1H).

Provenance & Evidence