Aluminium lithium hydride → 4-methyl-1-Oxa-4,9-diazaspiro[5.5]undecane

HRID 876057Notes

Reaction equation

HRID 876057 reaction equation
C1C2C(CO[C:16]([N:18]3[CH2:23][C:22]4([CH2:28][CH2:27][NH:26][CH2:25][CH2:24]4)[O:21][CH2:20][CH2:19]3)=O)C3C(=CC=CC=3)C=2C=CC=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH3:16][N:18]1[CH2:23][C:22]2([CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)[O:21][CH2:20][CH2:19]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 683226439H-fluoren-9-ylmethyl-1-oxa-4,9-diazaspiro[5.5]undecane-4-carboxylate

Product 1

HCID 217039594-methyl-1-Oxa-4,9-diazaspiro[5.5]undecaneYield 154.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of compound 404 (586.4 mg, 1.545 mmol) in tetrahydrofuran (20 mL) was added lithium aluminum hydride (240.5 mg, 6.34 mmol). After 1.5 hours at reflux the reaction was cooled to room temperature and quenched with water (240.5 μL), followed by 1N NaOH (240.5 μL), and then water (2×240.5 μL). The remaining solids were filtered off, and the filtrate was concentrated to give compound 405 (406 mg), as a sticky white solid. LCMS-ESI (POS), M/Z, M+1: Found 171.1, Calculated 171.1.

Workup

  1. temperatureAfter 1.5 hours at reflux the reaction
  2. customquenched with water (240.5 μL)
  3. filtrationThe remaining solids were filtered off
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-6c12a48354714a02aed2fe54ed45ce06
Source dataset
uspto-grants-2015_03
Patent number
US08980903B2

Reaction notes

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