Reacción #79579

Ecuación de reacción

(R)-(−)-1-amino-2-propanol

p-anisaldehyde

sodium triacetoxyborohydride

→

oil

Rendimiento 62.7%

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

Rendimiento 62.7%

Disolventes

tetrahydrofuran

acetic acid

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe solution was cooled in an ice-bath
2. 2
   workup.STIRRINGthe mixture was stirred at room temperature for 18 hours
3. 3
   ConcentraciónThe reaction mixture was concentrated under reduced pressure
4. 4
   Otrothe residue was partitioned between dichloromethane (150 ml) and sodium hydroxide solution (150 ml, 0.5N)
5. 5
   OtroThe layers were separated
6. 6
   Extracciónextracted with further dichloromethane (3×30 ml)
7. 7
   SecadoThe combined organic solutions were dried (MgSO4)
8. 8
   Otroevaporated under reduced pressure
9. 9
   OtroThe residue was purified by chromatography on silica gel (gradient elution 98:2:0.2 to 97:3:0.3 dichloromethane:methanol:0.88 NH3)

Procedimiento

A solution of (R)-(−)-1-amino-2-propanol (9.00 g, 0.12 mol) in tetrahydrofuran (40 ml) and acetic acid (5 ml) was added dropwise to a solution of p-anisaldehyde (5.45 g, 0.04 mol) in tetrahydrofuran (40 ml), and once addition was complete, the solution was stirred at room temperature for 2 hours. The solution was cooled in an ice-bath, and sodium triacetoxyborohydride (9.50 g, 0.0.045 mol) was added portionwise, and then the mixture was stirred at room temperature for 18 hours. The reaction mixture was concentrated under reduced pressure and the residue was partitioned between dichloromethane (150 ml) and sodium hydroxide solution (150 ml, 0.5N). The layers were separated and the aqueous phase was saturated with sodium chloride, then extracted with further dichloromethane (3×30 ml). The combined organic solutions were dried (MgSO4) and evaporated under reduced pressure. The residue was purified by chromatography on silica gel (gradient elution 98:2:0.2 to 97:3:0.3 dichloromethane:methanol:0.88 NH3) to afford an orange oil (4.9 g). 1H-NMR (CDCl3, 400 MHz) δ: 1.12 (d, 3H), 2.39 (dd, 1H), 2.70 (dd, 1H), 3.62-3.79 (m, 6H), 6.82 (d, 2H), 7.19 (d, 2H). LRMS: m/z (ES+) 196 [MH+].

Fuente