反応 #155399

反応方程式

Na2S2O3

3-(Boc-amino)-1-propanol

Dess-Martin reagent

→

N-Boc-3-amino-propanal

収率 86.8%

溶媒

NaHCO3

ether

water

反応条件

後処理

1. 1
   workup.STIRRINGThe reaction was stirred vigorously for 30 minutes until two layers
2. 2
   その他formed
3. 3
   ろ過The reaction was filtered
4. 4
   その他to remove the precipitated solids
5. 5
   抽出the aqueous layer was extracted with ether (1.0 L)
6. 6
   洗浄The organic layer was washed with sat. NaHCO3 (1.0 L), H2O (1.0 L), and brine (1 L)
7. 7
   乾燥dried over Na2SO4
8. 8
   濃縮concentrated to a clear oil
9. 9
   workup.DISSOLUTIONThe crude oil was dissolved in EtOAc:hexanes (1:1 v/v, 1.0 L)
10. 10
    ろ過filtered through a short silica gel column

実験手順

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).

出典