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

HRID 79234Notes

Reaction equation

HRID 79234 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-7269379e710c45c5a00baa444b30f3f4
Source dataset
uspto-grants-2014_09
Patent number
US08841312B2

Reaction notes

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