反応 #674300

反応方程式

NaHCO3

tert-butyl 2-oxo-7-azaspiro[3.5]nonane-7-carboxylate

sodium borohydride

→

tert-butyl 2-hydroxy-7-azaspiro[3.5]nonane-7-carboxylate

収率 57.0%

溶媒

MeOH

反応条件

後処理

1. 1
   濃縮The solution was concentrated by evaporator
2. 2
   その他to give the white solid
3. 3
   抽出The aqueous phase was extracted with DCM (4×30 mL)
4. 4
   乾燥The combined organic phase was dried over anhydrous Na2SO4
5. 5
   濃縮concentrated
6. 6
   その他to give the crude which
7. 7
   その他was purified by CombiFlash (24 g silica gel column, EtOAc/Hexane=0-60%)

実験手順

To a solution of tert-butyl 2-oxo-7-azaspiro[3.5]nonane-7-carboxylate (600 mg, 2.5 mmol, 1.0 equiv) in MeOH (6.0 mL) was added sodium borohydride (190 mg, 5.0 mmol, 2.0 equiv) in portions at 0° C. under nitrogen. The mixture was stirred at room temperature for 2.0 hrs. The solution was concentrated by evaporator to give the white solid. Saturated NaHCO3 solution (40 mL) was added. The aqueous phase was extracted with DCM (4×30 mL). The combined organic phase was dried over anhydrous Na2SO4, concentrated to give the crude which was purified by CombiFlash (24 g silica gel column, EtOAc/Hexane=0-60%) to afford 334 mg (yield 57%) of tert-butyl 2-hydroxy-7-azaspiro[3.5]nonane-7-carboxylate as a white solid.

出典