Reacción #79581

Ecuación de reacción

(R)-(−)-2-Amino-1-propanol

p-anisaldehyde

Acetic acid

sodium triacetoxyborohydride

→

ammonia

title compound

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

Disolventes

methanol

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturathe solution was cooled in an ice-bath
2. 2
   TemperaturaThe solution was warmed to 40° C.
3. 3
   Concentraciónthen concentrated under reduced pressure
4. 4
   OtroThe residue was partitioned between saturated sodium bicarbonate solution (50 ml) and dichloromethane (100 ml)
5. 5
   Otrothe layers were separated
6. 6
   ExtracciónThe aqueous phase was extracted with further dichloromethane (10×50 ml)
7. 7
   Secadothe combined organic solutions were dried (MgSO4)
8. 8
   Otroevaporated under reduced pressure
9. 9
   OtroThe residue was purified twice by column chromatography on silica gel using an elution gradient of dichloromethane

Procedimiento

(R)-(−)-2-Amino-1-propanol (10.36 ml, 133 mmol) was added dropwise to a solution of p-anisaldehyde (5.85 g, 42.9 mmol) in methanol (90 ml), and the solution was cooled in an ice-bath. Acetic acid (2.5 ml) and sodium triacetoxyborohydride (10.0 g, 47.2 mmol) were added and the reaction mixture was allowed to warm to room temperature over an hour. The solution was warmed to 40° C. and stirred for a further 48 hours then concentrated under reduced pressure. The residue was partitioned between saturated sodium bicarbonate solution (50 ml) and dichloromethane (100 ml) and the layers were separated. The aqueous phase was extracted with further dichloromethane (10×50 ml), and the combined organic solutions were dried (MgSO4) and evaporated under reduced pressure. The residue was purified twice by column chromatography on silica gel using an elution gradient of dichloromethane:methanol:0.88 ammonia (97:3:0.3 to 90:10:1) to afford the title compound, 6.0 g. 1H-NMR (CDCl3, 400 MHz) δ: 1.04 (d, 3H), 2.80 (m, 1H), 322 (dd, 1H), 3.58 (dd, 1H), 3.62 (d, 1H), 3.78 (m, 4H), 6.82 (d, 2H), 7.20 (d, 2H). LRMS: m/z (ES+) 196 [MH+]. [α]D=−34.85 (c=0.137, methanol)

Fuente