Aluminium lithium hydride → HCID 69180016, compound

HRID 2055738Notes

Reaction equation

HRID 2055738 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[N:7]([C:10]1([C:20]2[CH:24]=[CH:23][S:22][CH:21]=2)[CH2:19][CH2:18][C:13]2([O:17][CH2:16][CH2:15][O:14]2)[CH2:12][CH2:11]1)=[C:8]=O>C1COCC1>[CH3:8][NH:7][C:10]1([C:20]2[CH:24]=[CH:23][S:22][CH:21]=2)[CH2:19][CH2:18][C:13]2([O:14][CH2:15][CH2:16][O:17]2)[CH2:12][CH2:11]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydride2×HCID 86600443HCID 86600443, compound

Product 1

HCID 69180016HCID 69180016, compoundYield 43.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminium hydride (1.7 g) was added batchwise to 8-isocyanato-8-thiophen-3-yl-1,4-dioxa-spiro[4.5]decane (6 g; 22.6 mmole) dissolved in dry THF (70 ml) at 0 to 5° C. The reaction mixture was stirred for about 1.5 hours under reflux. On completion of the reaction (reaction monitored by thin layer chromatography), excess lithium aluminium hydride was destroyed with saturated aqueous sodium sulfate solution (20 ml). The resultant precipitate was filtered out over Celite. The filtrate was concentrated and extracted with ethyl acetate (3×100 ml). The organic phase was separated, dried (sodium sulfate) and concentrated under vacuum. Purification by column chromatography (silica gel, 50% ethyl acetate in n-hexane) yielded 2.5 g methyl-(8-thiophen-3-yl-1,4-dioxa-spiro[4.5]dec-8-yl)-amine (43%; white low-melting solid).

Workup

  1. temperatureunder reflux
  2. customwas destroyed with saturated aqueous sodium sulfate solution (20 ml)
  3. filtrationThe resultant precipitate was filtered out over Celite
  4. concentrationThe filtrate was concentrated
  5. extractionextracted with ethyl acetate (3×100 ml)
  6. customThe organic phase was separated
  7. dry with materialdried (sodium sulfate)
  8. concentrationconcentrated under vacuum
  9. customPurification by column chromatography (silica gel, 50% ethyl acetate in n-hexane)

Sources & evidence

ORD record
ord-0514aa48071c4023b236cdba51412ec8
Source dataset
uspto-grants-2008_02
Patent number
US07332519B2

Reaction notes

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