Reaction #674292

Reaction equation

NaHCO3

tert-butyl 6-oxo-2-azaspiro[3.3]heptane-2-carboxylate

NaBH4

→

tert-butyl 6-hydroxy-2-azaspiro[3.3]heptane-2-carboxylate

Yield 100.0%

Solvents

MeOH

Conditions

Workup

1. 1
   ConcentrationThe solution was concentrated by evaporator in vacuo
2. 2
   Otherto give crude solid
3. 3
   ExtractionThe aqueous mixture was extracted with DCM (4×30 mL)
4. 4
   DryingThe combined organic solution was dried over anhydrous Na2SO4
5. 5
   Concentrationconcentrated by evaporation in vacuo

Procedure

To a solution of tert-butyl 6-oxo-2-azaspiro[3.3]heptane-2-carboxylate (507 mg, 2.4 mmol) in MeOH (5.0 mL) was added NaBH4 (182 mg, 4.8 mmol) at 0° C. under N2. It was stirred at 0° C. for 30 min. The solution was concentrated by evaporator in vacuo to give crude solid. A saturated solution of NaHCO3 (30 mL) was added. The aqueous mixture was extracted with DCM (4×30 mL). The combined organic solution was dried over anhydrous Na2SO4 and then concentrated by evaporation in vacuo to afford tert-butyl 6-hydroxy-2-azaspiro[3.3]heptane-2-carboxylate (511 mg, 100%) as a white solid.

Source