تفاعل #43536

معادلة التفاعل

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

Dess-Martin periodinane

Sodium bisulfite

→

desired product

المردود 92.0%

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

المردود 92.0%

المذيبات

methylene chloride

ethyl acetate

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

(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).

المصدر