Aluminium lithium hydride → 1,4-Dioxa-10-azadispiro[4.2.4.2]tetradecane

HRID 1477952Notes

Reaction equation

HRID 1477952 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[O:7]1[C:11]2([CH2:21][CH2:20][C:14]3([CH2:18][CH2:17][NH:16][C:15]3=O)[CH2:13][CH2:12]2)[O:10][CH2:9][CH2:8]1>C1COCC1>[O:7]1[C:11]2([CH2:21][CH2:20][C:14]3([CH2:18][CH2:17][NH:16][CH2:15]3)[CH2:13][CH2:12]2)[O:10][CH2:9][CH2:8]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 582301081,4-Dioxa-10-azadispiro[4.2.4.2]tetradecan-9-one

Product 1

HCID 826579751,4-Dioxa-10-azadispiro[4.2.4.2]tetradecaneYield 94.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of LiAlH4 (21 g, 558.56 mmol) in anhydrous THF (500 mL) was added a solution of 1,4-dioxa-10-aza-dispiro[4.2.4.2]tetradecan-9-one (59 g, 279.28 mmol) in anhydrous THF (400 mL) dropwise at 0° C. in 1 h. The reaction mixture was heated to reflux and stirred for 2 h, then quenched with water at 0° C. until no bubble escaped and filtered. The filter cake was washed with a mixture of DCM and MeOH (1/1 (v/v), 500 mL). The filtrate was concentrated in vacuo and the residue was purified by silica gel column chromatography (MeOH/DCM (v/v)=1/10) to give the product as a yellow solid (52 g, 94%).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux
  3. customquenched with water at 0° C. until no bubble
  4. filtrationfiltered
  5. washThe filter cake was washed with a mixture of DCM and MeOH (1/1 (v/v), 500 mL)
  6. concentrationThe filtrate was concentrated in vacuo
  7. customthe residue was purified by silica gel column chromatography (MeOH/DCM (v/v)=1/10)

Sources & evidence

ORD record
ord-5329944405814987b99e8595a097e2d8
Source dataset
uspto-grants-2016_08
Patent number
US09403801B2

Reaction notes

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