Reaction #674300

Reaction equation

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

Yield 57.0%

Solvents

MeOH

Conditions

Workup

1. 1
   ConcentrationThe solution was concentrated by evaporator
2. 2
   Otherto give the white solid
3. 3
   ExtractionThe aqueous phase was extracted with DCM (4×30 mL)
4. 4
   DryingThe combined organic phase was dried over anhydrous Na2SO4
5. 5
   Concentrationconcentrated
6. 6
   Otherto give the crude which
7. 7
   Otherwas purified by CombiFlash (24 g silica gel column, EtOAc/Hexane=0-60%)

Procedure

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.

Source