반응 #48640

반응 방정식

sodium borohydride

(2R,5R)-5-[(1R,2S)-3-(3-chloro-5-fluorophenyl)-1-hydroxy-2-nitropropyl]-2-(2,2-dimethylpropoxy)-morpholine-4-carboxylic acid tert-butyl ester

→

desired compound

수율 100.0%

(2R,5R)-5-[(1S,2S)-2-Amino-3-(3-chloro-5-fluorophenyl)-1-hydroxypropyl]-2-(2,2-dimethylpropoxy)-morpholine-4-carboxylic acid tert-butyl ester

수율 100.0%

용매

methanol

반응 조건

후처리

1. 1
   workup.STIRRINGstir for 15 minutes
2. 2
   추출Add water (2 mL), 0.1 N sodium hydroxide (2 mL) and extract with ethyl acetate (2×30 mL)
3. 3
   세척Combine organic extracts, wash with saturated aqueous sodium chloride (30 mL)
4. 4
   건조dry (sodium sulfate)
5. 5
   여과filter through a pad of Celite®
6. 6
   농축concentrate

실험 절차

Dissolve (2R,5R)-5-[(1R,2S)-3-(3-chloro-5-fluorophenyl)-1-hydroxy-2-nitropropyl]-2-(2,2-dimethylpropoxy)-morpholine-4-carboxylic acid tert-butyl ester (0.455 g, 0.901 mmol) in methanol (8 mL) and stir at room temperature in an oil bath. Add anhydrous nickel (II) chloride (0.175 g, 1.35 mmol) followed by sodium borohydride (0.170 mg, 4.50 mmol) in 3 portions over 5 minutes and stir for 15 minutes. Add water (2 mL), 0.1 N sodium hydroxide (2 mL) and extract with ethyl acetate (2×30 mL). Combine organic extracts, wash with saturated aqueous sodium chloride (30 mL), dry (sodium sulfate), filter through a pad of Celite® and concentrate to give the desired compound as a colorless oil (0.428 g).

출처