Reaction #166413

Reaction equation

lithium aluminum hydride

compound 399

9-benzyl-1-oxa-4,9-diazaspiro[5.5]undecan-3-one

→

compound 402

Yield 82.7%

9-benzyl-1-oxa-4,9-diazaspiro[5.5]undecane

Yield 82.7%

Solvents

tetrahydrofuran

Conditions

Workup

1. 1
   TemperatureAfter 1.25 hours of reflux the reaction
2. 2
   Otherquenched with water (2.22 mL)
3. 3
   FiltrationThe remaining solids were filtered off
4. 4
   Concentrationthe filtrate was concentrated

Procedure

To a stirring mixture of lithium aluminum hydride (2.22 g, 58.5 mmol) in tetrahydrofuran (70 mL) was added compound 399 (3.60 g, 13.8 mmol), portionwise over three minutes. After 1.25 hours of reflux the reaction was cooled to room temperature and quenched with water (2.22 mL), then 1N NaOH (2.22 mL), then water (2×2.22 mL). The remaining solids were filtered off, and the filtrate was concentrated to give compound 402 (2.81 g, 82%). LCMS-ESI (POS), M/Z, M+1: Found 247.1, Calculated 247.2.

Source