Tetrahydrofuran → 8-Azaspiro(4.5)decane

HRID 1744818Notes

Reaction equation

HRID 1744818 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].ClCCl.[CH3:10]O.C([N:14]([CH2:17][CH3:18])[CH2:15][CH3:16])C.O1[CH2:23][CH2:22][CH2:21][CH2:20]1>>[CH2:20]1[C:10]2([CH2:16][CH2:15][NH:14][CH2:17][CH2:18]2)[CH2:23][CH2:22][CH2:21]1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 21226445Aluminium lithium hydrideHCID 21913430dichloromethane MeOH Et3N

Product 1

HCID 4371528-Azaspiro(4.5)decaneYield 95%

Procedure

Was prepared from (3,3-pentamethylenglutarimide by lithium aluminium hydride reduction in tetrahydrofurane under standard conditions. Flash chromatography (silica, eluent dichloromethane/methanol/triethylamine 10:2:0.1) afforded the title compound as light yellow oil (>95% yield). MS 154(M+H+).

Sources & evidence

ORD record
ord-c943fc3f1bb14d4d9b585a6d5cb9aa84
Source dataset
uspto-grants-2006_03
Patent number
US07019001B2

Reaction notes

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