반응 #11801

반응 방정식

(2-Amino-ethyl)-carbamic acid tert-butyl ester

4-fluorobenzaldehyde

triethylamine

magnesium sulfate

sodium borohydride

→

title compound

수율 75.2%

[2-(4-fluoro-benzylamino)-ethyl]-carbamic acid tert-butyl ester

수율 75.2%

용매

methanol

반응 조건

후처리

1. 1
   기타After 2 h the reaction was quenched with water
2. 2
   추출extracted three times with ethyl acetate
3. 3
   세척The combined organic layers were washed three times with water
4. 4
   추출the desired product extracted into the aqueous layer with 0.5 M hydrochloric acid (4×50 mL)
5. 5
   세척The combined acid wash
6. 6
   온도was cooled to 0° C.
7. 7
   추출The aqueous layer was extracted three times with chloroform
8. 8
   세척the combined chloroform layer washed three times with water
9. 9
   건조dried over sodium sulfate
10. 10
    농축concentrated

실험 절차

(2-Amino-ethyl)-carbamic acid tert-butyl ester (5.95 g, 37.1 mmol), 4-fluorobenzaldehyde (5.07 g, 40.9 mmol, 4.4 mL), triethylamine (1.50 g, 14.9 mmol, 2.1 mL) and magnesium sulfate (6.71 g, 55.7 mmol) were stirred in methanol (50 mL). After 1.5 h the solution was cooled to 0° C. and sodium borohydride (8.4 g, 223 mmol) was added in portions. After 2 h the reaction was quenched with water and extracted three times with ethyl acetate. The combined organic layers were washed three times with water and the desired product extracted into the aqueous layer with 0.5 M hydrochloric acid (4×50 mL). The combined acid wash was cooled to 0° C. and basified with saturated aqueous ammonium hydroxide. The aqueous layer was extracted three times with chloroform and the combined chloroform layer washed three times with water, dried over sodium sulfate and concentrated to yield the title compound as a colorless oil (7.49 g).

출처