Reacción #41280

Ecuación de reacción

3-amino -1-propanol

aldehyde

9-anthraldehyde

NaBH4

→

product 14a

Rendimiento 78.0%

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

Rendimiento 78.0%

Disolventes

MeOH CH2Cl2

MeOH CH2Cl2

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe solvent was removed in vacuo
2. 2
   workup.DISSOLUTIONthe solid residue dissolved in 50% MeOH/CH2Cl2 (40 mL)
3. 3
   OtroThe solvent was removed in vacuo
4. 4
   workup.DISSOLUTIONthe solid residue dissolved in CH2Cl2 (40 mL)
5. 5
   Lavadowashed with 10% aq. Na2CO3 solution (3×30 mL)
6. 6
   OtroThe CH2Cl2 layer was separated
7. 7
   Secadodried over anhydrous Na2SO4
8. 8
   Filtraciónfiltered
9. 9
   Otroremoved in vacuo
10. 10
    Otroto give an oily residue
11. 11
    OtroThe oil was purified by flash column chromatography (6% MeOH/CHCl3)

Procedimiento

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).

Fuente