Aluminium lithium hydride → HCID 53629211, compound

HRID 1924336Notes

Reaction equation

HRID 1924336 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[F:7][C:8]1[CH:9]=[C:10]2[N:15]([C:16]=1[C:17]#[N:18])[CH:14]=[CH:13][CH:12]=[CH:11]2>CCOCC>[F:7][C:8]1[CH:9]=[C:10]2[N:15]([C:16]=1[CH2:17][NH2:18])[CH:14]=[CH:13][CH:12]=[CH:11]2

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 45088639HCID 45088639, compound

Product 1

HCID 53629211HCID 53629211, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

LiAlH4 (0.175 g, 4.6 mmol) is added in portions under stirring in argon to a solution of 2-fluoroindolizine-3-carbonitrile x262 [X. Fang, Y.-M. Wu, J. Deng, S.-W. Wang, Tetrahedron 2004, 60, 5487-5493] (0.46 g, 2.9 mmol) in absolute ether (15 ml) for 3 min. The reaction mixture is stirred at room temperature for 30 min, cooled to 0-5° C., and quenched by the addition of a 10% NaOH solution (4 ml). The organic layer is separated, and the aqueous layer is subjected to extraction with ether (3×10 ml). The combined organic extracts are dried over anhydrous Na2SO4. The solvents are removed reduced pressure to give 1-(2-fluoroindolizin-3-yl)methanamine x263 (0.38 g).

Workup

  1. temperaturecooled to 0-5° C.
  2. customquenched by the addition of a 10% NaOH solution (4 ml)
  3. customThe organic layer is separated
  4. extractionthe aqueous layer is subjected to extraction with ether (3×10 ml)
  5. dry with materialThe combined organic extracts are dried over anhydrous Na2SO4
  6. customThe solvents are removed reduced pressure

Sources & evidence

ORD record
ord-70fd7ea59f67479fb2c37e1c64157ff7
Source dataset
uspto-grants-2012_05
Patent number
US08178533B2

Reaction notes

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