Reacción #155399

Ecuación de reacción

Na2S2O3

3-(Boc-amino)-1-propanol

Dess-Martin reagent

→

N-Boc-3-amino-propanal

Rendimiento 86.8%

Disolventes

NaHCO3

ether

water

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGThe reaction was stirred vigorously for 30 minutes until two layers
2. 2
   Otroformed
3. 3
   FiltraciónThe reaction was filtered
4. 4
   Otroto remove the precipitated solids
5. 5
   Extracciónthe aqueous layer was extracted with ether (1.0 L)
6. 6
   LavadoThe organic layer was washed with sat. NaHCO3 (1.0 L), H2O (1.0 L), and brine (1 L)
7. 7
   Secadodried over Na2SO4
8. 8
   Concentraciónconcentrated to a clear oil
9. 9
   workup.DISSOLUTIONThe crude oil was dissolved in EtOAc:hexanes (1:1 v/v, 1.0 L)
10. 10
    Filtraciónfiltered through a short silica gel column

Procedimiento

To a stirring solution of 3-(Boc-amino)-1-propanol (25 mL, 0.144 mol) in water saturated DCM (1.0 L) was added Dess-Martin reagent (99.2 g, 233.9 mmol) and the reaction mixture was stirred for 1 hour. The reaction was then diluted with ether (1.0 L), followed by a solution of Na2S2O3 (250 g) in 80% NaHCO3 (450 g in 1.0 L H2O). The reaction was stirred vigorously for 30 minutes until two layers formed, the top layer was clear. The reaction was filtered to remove the precipitated solids and the aqueous layer was extracted with ether (1.0 L). The organic layer was washed with sat. NaHCO3 (1.0 L), H2O (1.0 L), and brine (1 L), dried over Na2SO4 and concentrated to a clear oil. The crude oil was dissolved in EtOAc:hexanes (1:1 v/v, 1.0 L) and filtered through a short silica gel column to yield the desired N-Boc-3-amino-propanal (21.7 g, 0.125 mol, 85.6% yield): 1H NMR (400 MHz, CDCl3) δ 9.77 (s, 1H, CHO), 4.85 (bs, 1H, NH), 3.36-3.42 (m, 2H, CH2), 2.67 (t, 2H, CH2), 1.39 (s, 9H, (CH3)3).

Fuente