Reaktion #43536

Reaktionsgleichung

(S)-(−)-2-(tert-Butoxycarbonylamino)-1-propanol

Dess-Martin periodinane

Sodium bisulfite

→

desired product

Ausbeute 92.0%

(S)-2-(tert-Butoxycarbonylamino)-propionaldehyde

Ausbeute 92.0%

Lösungsmittel

methylene chloride

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe reaction to completion
2. 2
   Sonstigethe organic layer was separated
3. 3
   WaschenThe aqueous layer was washed with 3×30 mL EtOAc
4. 4
   WaschenThe combined organic layers were washed with 50 mL 1 M NaOH
5. 5
   Trocknendried over MgSO4
6. 6
   FiltrationFiltration and rotary evaporation

Vorschrift

(S)-(−)-2-(tert-Butoxycarbonylamino)-1-propanol (523 mg, 2.98 mmol, 1.0 equiv.) was dissolved in 45 mL methylene chloride in a 100 mL r.b. flask with a magnetic stir bar. To this clear homogeneous solution, Dess-Martin periodinane (1.523 g, 3.591 mmol, 1.2 equiv.) was added in one portion and the cloudy white reaction mixture was allowed to stir at room temperature for 2 h. Thin-layer chromotography monitored the reaction to completion. The reaction mixture was diluted with 100 mL ethyl acetate. Sodium bisulfite solution (2 M, 20 mL) was added to the reaction mixture and the organic layer was separated. The aqueous layer was washed with 3×30 mL EtOAc. The combined organic layers were washed with 50 mL 1 M NaOH, followed by saturated NaCl (30 mL) and dried over MgSO4. Filtration and rotary evaporation produced the desired product as a yellow oil (475 mg, 92% yield, Rf=0.63, 1:1 hexanes/ethyl acetate).

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