Reaction #155399

Reaction equation

Na2S2O3

3-(Boc-amino)-1-propanol

Dess-Martin reagent

→

N-Boc-3-amino-propanal

Yield 86.8%

Solvents

NaHCO3

ether

water

Conditions

Workup

1. 1
   workup.STIRRINGThe reaction was stirred vigorously for 30 minutes until two layers
2. 2
   Otherformed
3. 3
   FiltrationThe reaction was filtered
4. 4
   Otherto remove the precipitated solids
5. 5
   Extractionthe aqueous layer was extracted with ether (1.0 L)
6. 6
   WashThe organic layer was washed with sat. NaHCO3 (1.0 L), H2O (1.0 L), and brine (1 L)
7. 7
   Dryingdried 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

Procedure

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