Water → 1-{1,4-Dioxaspiro[4.5]decan-8-yl}methanamine

HRID 2396738Notes

Reaction equation

HRID 2396738 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[O:7]1[C:11]2([CH2:16][CH2:15][CH:14]([C:17]([NH2:19])=O)[CH2:13][CH2:12]2)[O:10][CH2:9][CH2:8]1.O.ClCCl>C1COCC1>[NH2:19][CH2:17][CH:14]1[CH2:15][CH2:16][C:11]2([O:7][CH2:8][CH2:9][O:10]2)[CH2:12][CH2:13]1

Participants

6

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 192616901,4-Dioxaspiro[4.5]decane-8-carboxamideHCID 21226445Aluminium lithium hydride

Product 1

HCID 109539781-{1,4-Dioxaspiro[4.5]decan-8-yl}methanamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 1.4 g (0.037 mole) of lithium aluminum hydride in 100 ml dry THF is added, portionwise, 4.9 g (0.026 mole) of 1,4-dioxaspiro[4,5]decane-8-carboxamide over one-half hour. This mixture is then refluxed 2 hours, then allowed to cool to room temperature. About 5 ml water is added cautiously and then stirred 15 minutes. Dichloromethane is then added and the insolubles filtered off. The organic layer is dried over MgSO4 and stripped to dryness, giving 3.48 g crude product. This material is vacuum-distilled to obtain 8-aminomethyl-1,4-dioxaspiro[4,5]decane (b.p. 84°-101° C. at 0.7 mm Hg.)

Workup

  1. temperatureThis mixture is then refluxed 2 hours
  2. filtrationthe insolubles filtered off
  3. dry with materialThe organic layer is dried over MgSO4
  4. customgiving 3.48 g crude product
  5. distillationThis material is vacuum-distilled

Sources & evidence

ORD record
ord-9360af0fbdac4df2ab78c9459014c2de
Source dataset
uspto-grants-1996_02
Patent number
US05494918

Reaction notes

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