反应 #7285

反应方程式

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

aniline

acetic acid

NaBH(OAc)3

→

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

收率 9.0%

溶剂

CH2Cl2

THF

反应条件

后处理

1. 1
   其他overnight
2. 2
   洗涤washed with saturated aqueous NaHCO3 (50 mL)
3. 3
   洗涤The aqueous phase was washed with CH2Cl2 (2×25 mL)
4. 4
   干燥the combined organic extracts dried (Na2SO4)
5. 5
   过滤filtered
6. 6
   浓缩concentrated under reduced pressure
7. 7
   其他Purification and separation of the resultant brown oil by flash chromatography on silica gel (Hexanes/EtOAc, 9:1)

实验过程

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.

来源