Isobutylene oxide → 4-Aza-4-butyl-2,2-dimethyl-1-oxaspiro[4.5]decane

HRID 650254Notes

Reaction equation

HRID 650254 reaction equation
[C:1]1(=[CH:7][CH2:8][CH2:9][CH2:10][NH2:11])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[O:12]1[C:14]([CH3:16])([CH3:15])[CH2:13]1.[I-].[Sm+2].[I-]>O1CCCC1>[CH2:8]([CH:7]1[C:1]2([CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[O:12][C:14]([CH3:16])([CH3:15])[CH2:13]1)[CH2:9][CH2:10][NH2:11]

Participants

5

Reactant 3

HCID 11208Isobutylene oxideHCID 19875469N-cyclohexylidenebutylamineHCID 178506586HCID 178506586, compound

Product 1

HCID 217147314-Aza-4-butyl-2,2-dimethyl-1-oxaspiro[4.5]decaneYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1 mmol of N-cyclohexylidenebutylamine, 2 mmol of 1,2-epoxy-2-methylpropane, 0.05 mmol of samarium(II) iodide (SmI2), and 1 ml of tetrahydrofuran was stirred at room temperature for 5 hours. Products in the reaction mixture was isolated through column chromatography to yield 4-aza-4-butyl-2,2-dimethyl-1-oxaspiro[4.5]decane of the following formula in yield of 85%.

Workup

  1. customProducts in the reaction mixture was isolated through column chromatography

Sources & evidence

ORD record
ord-7d0f853d06584fc1b3a914b49da0af2d
Source dataset
uspto-grants-2001_08
Patent number
US06271387B1

Reaction notes

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