Réaction #7285

Équation de réaction

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

aniline

acetic acid

NaBH(OAc)3

→

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

Rendement 9.0%

Solvants

CH2Cl2

THF

Conditions de réaction

Traitement

1. 1
   Autreovernight
2. 2
   Lavagewashed with saturated aqueous NaHCO3 (50 mL)
3. 3
   LavageThe aqueous phase was washed with CH2Cl2 (2×25 mL)
4. 4
   Séchagethe combined organic extracts dried (Na2SO4)
5. 5
   Filtrationfiltered
6. 6
   Concentrationconcentrated under reduced pressure
7. 7
   AutrePurification and separation of the resultant brown oil by flash chromatography on silica gel (Hexanes/EtOAc, 9:1)

Mode opératoire

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.

Source