9-Benzyl-1-oxa-4,9-diazaspiro[5.5]undecan-3-one → 9-Benzyl-1-oxa-4,9-diazaspiro[5.5]undecane

HRID 876054Notes

Reaction equation

HRID 876054 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([N:14]1[CH2:25][CH2:24][C:17]2([O:22][CH2:21][C:20](=O)[NH:19][CH2:18]2)[CH2:16][CH2:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>O1CCCC1>[CH2:7]([N:14]1[CH2:15][CH2:16][C:17]2([O:22][CH2:21][CH2:20][NH:19][CH2:18]2)[CH2:24][CH2:25]1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 205220419-Benzyl-1-oxa-4,9-diazaspiro[5.5]undecan-3-oneHCID 21226445Aluminium lithium hydride

Product 1

HCID 357537449-Benzyl-1-oxa-4,9-diazaspiro[5.5]undecaneYield 82.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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.

Workup

  1. temperatureAfter 1.25 hours of reflux the reaction
  2. customquenched with water (2.22 mL)
  3. filtrationThe remaining solids were filtered off
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-2dcc43ea69014a0ebf47a4682f6e2514
Source dataset
uspto-grants-2015_03
Patent number
US08980903B2

Reaction notes

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