Reaction #43536

Reaction equation

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

Dess-Martin periodinane

Sodium bisulfite

→

desired product

Yield 92.0%

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

Yield 92.0%

Solvents

methylene chloride

ethyl acetate

Conditions

Workup

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

Procedure

(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).

Source