반응 #7285

반응 방정식

2-[N-(t-butyloxycarbonyl)]amino-cyclohexanone

aniline

acetic acid

NaBH(OAc)3

→

cis-N-phenyl-N′-(t-butyloxycarbonyl)-cyclohexane-1,2-diamine

수율 9.0%

용매

CH2Cl2

THF

반응 조건

후처리

1. 1
   기타overnight
2. 2
   세척washed with saturated aqueous NaHCO3 (50 mL)
3. 3
   세척The aqueous phase was washed with CH2Cl2 (2×25 mL)
4. 4
   건조the combined organic extracts dried (Na2SO4)
5. 5
   여과filtered
6. 6
   농축concentrated under reduced pressure
7. 7
   기타Purification and separation of the resultant brown oil by flash chromatography on silica gel (Hexanes/EtOAc, 9:1)

실험 절차

To a solution of 2-[N-(t-butyloxycarbonyl)]amino-cyclohexanone (0.785 g, 3.69 mmol, aniline (0.68 mL, 7.46 mmol) and glacial acetic acid (0.22 mL) in THF (10 mL) was added NaBH(OAc)3 (1.173 g, 5.53 mmol) and the mixture was stirred at 60□ C. overnight. The reaction was cooled to room temperature, diluted with CH2Cl2 (60 mL) and washed with saturated aqueous NaHCO3 (50 mL). The aqueous phase was washed with CH2Cl2 (2×25 mL) and the combined organic extracts dried (Na2SO4), filtered and concentrated under reduced pressure. Purification and separation of the resultant brown oil by flash chromatography on silica gel (Hexanes/EtOAc, 9:1) afforded the low polarity cis-N-phenyl-N′-(t-butyloxycarbonyl)-cyclohexane-1,2-diamine isomer (0.095 g, 9%) and the high polarity trans-N-phenyl-N′-(t-butyloxycarbonyl)-cyclohexane-1,2-diamine isomer (0.412 g, 39%), both as pale yellow solids.

출처