反応 #56778

反応方程式

N-(t-butyloxycarbonyl)cyclohexylglycine

THF

Borane

→

tert-butyl 1-cyclohexyl-2-hydroxyethylcarbamate

収率 66.7%

反応条件

後処理

1. 1
   その他The reaction was quenched with MeOH (5 mL), volatiles
2. 2
   その他were evaporated
3. 3
   その他the residue was partitioned between water and EtOAc
4. 4
   洗浄The organic layer was washed with saturated NaHCO3/water, brine
5. 5
   乾燥dried (sodium sulfate)
6. 6
   その他evaporated

実験手順

A solution of N-(t-butyloxycarbonyl)cyclohexylglycine (2.0 g, 7.77 mmol) in anhydrous THF (10 mL) was cooled to 0° C. Borane solution (1 M in THF, 15.5 mL, 15.5 mmol) was added slowly and the reaction mixture was warmed to room temperature and stirred for 2 hours. The reaction was quenched with MeOH (5 mL), volatiles were evaporated and the residue was partitioned between water and EtOAc. The organic layer was washed with saturated NaHCO3/water, brine, dried (sodium sulfate), and evaporated to give tert-butyl 1-cyclohexyl-2-hydroxyethylcarbamate 4a (1.26 g, 66.7%), MS (CI) m/z 144.2 (MH+-Boc).

出典