反应详情

(R)-N,N-Diisopropyl-3-(5-formyl-2-hydroxyphenyl)-3-phenylpropanamine (prepared in Example 7.1) (1.23 g, 3.62 mmol) was dissolved in methanol (20 mL). Ethylamine [3.62 mL, 21.7 mmol (6M hydrochloric acid in methanol)] and sodium cyanoborohydride (0.14 g, 2.17 mmol) were added. The mixture was stirred overnight at room temperature. The solvent was evaporated and the residue was chromatographed on silica (toluene-ethyl acetate-triethylamine 7:3:1). The product was dissolved in diethyl ether and hydrogen chloride in diethyl ether was added. The resulting oil was stirred in diethyl ether over night to give crystals. Yield 0.70 g (44%); mp. 140-142° C.; [α]D−5.0° (c=0.5, methanol); 1H NMR (CD3OD) δ1.30 (m, 15H), 2.59 (m, 2H), 3.05 (m, 4H), 3.70 (m, 2H), 4.07 (s, 2H), 4.42 (t, 1H), 6.85 (d, 1H), 7.20 (m, 2H), 7.30 (t, 2H), 7.41 (d, 2H), 7.50 (s, 1H) Anal. (C24H36N2O*2.0 HCl*0.5H2O) C,H,N.

1. customThe solvent was evaporated
2. customthe residue was chromatographed on silica (toluene-ethyl acetate-triethylamine 7:3:1)
3. dissolutionThe product was dissolved in diethyl ether
4. additionhydrogen chloride in diethyl ether was added
5. stirringThe resulting oil was stirred in diethyl ether over night
6. customto give crystals