Réaction #155399

Équation de réaction

Na2S2O3

3-(Boc-amino)-1-propanol

Dess-Martin reagent

→

N-Boc-3-amino-propanal

Rendement 86.8%

Solvants

NaHCO3

ether

water

Conditions de réaction

Traitement

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

Mode opératoire

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).

Source