Yield:14131-13-6 78%

Reaction Conditions:

Stage #1: 9-anthracene aldehyde;propan-1-ol-3-amine in methanol;dichloromethane at 20;
Stage #2: with sodium tetrahydroborate in methanol;dichloromethane at 0 - 20;

Steps:

14 Synthesis of 3-[(Anthracen-9-ylmethyl)-amino]-propan-1-ol, 14a

To a stirred solution of 3-amino -1-propanol, 15a (0.87 g, 11.65 mmol) in 25% MeOH/CH₂Cl₂ (20 mL), was added a solution of aldehyde 8 (2.00 g, 9.7 mmol) in 25% MeOH/CH₂Cl₂ (15 mL) under N₂. The mixture was stirred at room temperature overnight until the imine formation was complete (monitored by NMR). The solvent was removed in vacuo, the solid residue dissolved in 50% MeOH/CH₂Cl₂ (40 mL) and the solution was cooled to 0° C. NaBH₄ (29.1 mmol) was added in small portions to the solution and the mixture was stirred at rt overnight. The solvent was removed in vacuo, the solid residue dissolved in CH₂Cl₂ (40 mL) and washed with 10% aq. Na₂CO₃ solution (3×30 mL). The CH₂Cl₂ layer was separated, dried over anhydrous Na₂SO₄, filtered and removed in vacuo to give an oily residue. The oil was purified by flash column chromatography (6% MeOH/CHCl₃) to yield the product 14a as a pale yellow thick oil (78%), R_f=0.3 (6% MeOH/CHCl₃); ¹H NMR (CDCl₃) δ 8.39 (s, 1H), 8.27 (d, 2H), 7.99 (d, 2H), 7.52 (m, 2H), 7.45 (m, 2H), 4.71 (s, 2H), 3.79 (t, 2H), 3.09 (t, 2H), 1.74 (q, 2H).

References:

US2007/213397,2007,A1 Location in patent:Page/Page column 7