反応 #7285

反応方程式

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

aniline

acetic acid

NaBH(OAc)3

→

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

収率 9.0%

溶媒

CH2Cl2

THF

反応条件

後処理

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

実験手順

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.

出典