Reacción #79580

Ecuación de reacción

(S)-(+)-1-amino-2-propanol

p-anisaldehyde

acetic acid

sodium triacetoxyborohydride

→

ammonia

title compound

(2S)-1-[(4-Methoxybenzyl)amino]-2-propanol

Disolventes

methanol

Condiciones de reacción

Tratamiento posterior

1. 1
   ConcentraciónThe reaction mixture was concentrated under reduced pressure
2. 2
   Otrothe residue was partitioned between dichloromethane (150 ml) and sodium hydroxide solution (100 ml, 0.5N)
3. 3
   OtroThe layers were separated
4. 4
   Extracciónthe aqueous phase was extracted with further dichloromethane (4×30 ml)
5. 5
   SecadoThe combined organic solutions were dried (MgSO4)
6. 6
   Concentraciónconcentrated under reduced pressure
7. 7
   OtroThe residual yellow oil was purified by column chromatography on silica gel using an elution gradient of dichloromethane

Procedimiento

A mixture of (S)-(+)-1-amino-2-propanol (9 g, 0.12 mol), p-anisaldehyde (5.45 g, 0.04 mol), acetic acid (5 ml), and sodium triacetoxyborohydride (9.5 g, 0.045 mol) in methanol (80 ml) was stirred at room temperature for 72 hours. The reaction mixture was concentrated under reduced pressure and the residue was partitioned between dichloromethane (150 ml) and sodium hydroxide solution (100 ml, 0.5N). The layers were separated, and the aqueous phase was extracted with further dichloromethane (4×30 ml). The combined organic solutions were dried (MgSO4) and concentrated under reduced pressure. The residual yellow oil was purified by column chromatography on silica gel using an elution gradient of dichloromethane:methanol:0.88 ammonia (98:2:0.2 to 95:5:0.5) to afford the title compound, 6.2 g. 1H-NMR (CDCl3, 400 MHz) δ: 1.10 (d, 3H), 2.24-2.40 (m, 2H), 2.65 (dd, 1H), 3.62-3.80 (m, 6H), 6.82 (d, 2H), 7.19 (d, 2H). LRMS: m/z (ES+) 218 [MNa+]

Fuente