반응 #2340157

반응 방정식

water

N-BOC-(R)-2-(4-hydroxybenzyl)morpholine

N-bromosuccinimide

→

N-BOC-(R)-2-(3-bromo-4-hydroxybenzyl)morpholine

용매

N,N-dimethyl formamide

반응 조건

후처리

1. 1
   추출extracted with ethyl acetate (70 mL×2)
2. 2
   세척Combined organic layers were washed with water (2×50 mL), brine (50 mL)
3. 3
   건조dried (MgSO4)
4. 4
   여과filtered
5. 5
   농축concentrated in vacuo
6. 6
   농축The material was concentrated onto sodium sulfate
7. 7
   기타purified by column chromatography (silica; 17% ethyl acetate/isohexane)

실험 절차

To a stirred solution of intermediate (b), N-BOC-(R)-2-(4-hydroxybenzyl)morpholine (1.0 g, 3.41 mmol) in anhydrous N,N-dimethyl formamide (10 mL), under at atmosphere of nitrogen at room temperature was added N-bromosuccinimide (0.63 g, 3.58 mmol). The resulting solution was stirred at room temperature for 2 hrs and then poured into water (50 mL) and extracted with ethyl acetate (70 mL×2). Combined organic layers were washed with water (2×50 mL), brine (50 mL), dried (MgSO4), filtered and concentrated in vacuo. The material was concentrated onto sodium sulfate and purified by column chromatography (silica; 17% ethyl acetate/isohexane) to yield the desired intermediate (a), N-BOC-(R)-2-(3-bromo-4-hydroxybenzyl)morpholine, as a white solid (0.89 g).

출처