Aluminium lithium hydride → [4-(Aminomethyl)oxan-4-yl]methanol

HRID 1748303Notes

Reaction equation

HRID 1748303 reaction equation
[C:1]([C:3]1([C:9](OCC)=[O:10])[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1)#[N:2].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[NH2:2][CH2:1][C:3]1([CH2:9][OH:10])[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 22061355Ethyl 4-cyanooxane-4-carboxylate

Product 1

HCID 22379474[4-(Aminomethyl)oxan-4-yl]methanolYield 100.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of ethyl 4-cyanotetrahydro-2H-pyran-4-carboxylate (10 g, 54.64 mmol) in THF (50 mL) is added dropwise to a suspension of lithium aluminum hydride (8.26 g, 218.5 mmol) in THF (100 mL) at 0° C. The reaction mixture is warmed to room temperature and stirred for 4 h. The mixture is cooled to 0° C. and ice cold water (30 mL) is added slowly. The mixture is extracted with EtOAc (2×200 mL) and the organic layers are combined, dried (Na2SO4) and concentrated to afford the title crude compound (8 g, >99%) which is used in the next step without purification.

Workup

  1. temperatureThe mixture is cooled to 0° C.
  2. extractionThe mixture is extracted with EtOAc (2×200 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-584655cea25b483592af86f92908368b
Source dataset
uspto-grants-2015_10
Patent number
US09150577B2

Reaction notes

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