반응 #155399

반응 방정식

Na2S2O3

3-(Boc-amino)-1-propanol

Dess-Martin reagent

→

N-Boc-3-amino-propanal

수율 86.8%

용매

NaHCO3

ether

water

반응 조건

후처리

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

실험 절차

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).

출처