反応 #41280

反応方程式

3-amino -1-propanol

aldehyde

9-anthraldehyde

NaBH4

→

product 14a

収率 78.0%

3-[(Anthracen-9-ylmethyl)-amino]-propan-1-ol

収率 78.0%

溶媒

MeOH CH2Cl2

MeOH CH2Cl2

反応条件

後処理

1. 1
   その他The solvent was removed in vacuo
2. 2
   workup.DISSOLUTIONthe solid residue dissolved in 50% MeOH/CH2Cl2 (40 mL)
3. 3
   その他The solvent was removed in vacuo
4. 4
   workup.DISSOLUTIONthe solid residue dissolved in CH2Cl2 (40 mL)
5. 5
   洗浄washed with 10% aq. Na2CO3 solution (3×30 mL)
6. 6
   その他The CH2Cl2 layer was separated
7. 7
   乾燥dried over anhydrous Na2SO4
8. 8
   ろ過filtered
9. 9
   その他removed in vacuo
10. 10
    その他to give an oily residue
11. 11
    その他The oil was purified by flash column chromatography (6% MeOH/CHCl3)

実験手順

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%), Rf=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).

出典