Aluminium lithium hydride → HCID 59497624, compound

HRID 1747436Notes

Reaction equation

HRID 1747436 reaction equation
C[O:2][C:3]([C:5]1[C:13]2[N:9]([C:10]([CH3:15])=[C:11]([CH3:14])[CH:12]=2)[CH:8]=[CH:7][CH:6]=1)=O.[H-].[H-].[H-].[H-].[Li+].[Al+3]>CCOCC.C1COCC1>[CH3:14][C:11]1[CH:12]=[C:13]2[N:9]([C:10]=1[CH3:15])[CH:8]=[CH:7][CH:6]=[C:5]2[CH2:3][OH:2]

Participants

5

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 59497655HCID 59497655, compound

Product 1

HCID 59497624HCID 59497624, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of the 2,3-dimethyl-indolizine-8-carboxylic acid methyl ester (265 mg, 1.3 mmol) in ether (10 ml) was cooled to 0° C. and treated with LAH (1.0M in THF, 1.6 ml, 1.6 mmol, dropwise addition). After 3.5 h the reaction was quenched with sodium sulfate decahydrate (added in small portions until gas evolution ceased). The resulting mixture was stirred for 0.5 h and the precipitated solids were removed via filtration and washed with EtOAc. The combined filtrates were concentrated to give the product which was used without further purification.

Workup

  1. addition1.6 ml, 1.6 mmol, dropwise addition)
  2. customAfter 3.5 h the reaction was quenched with sodium sulfate decahydrate (added in small portions until gas evolution ceased)
  3. customthe precipitated solids were removed via filtration
  4. washwashed with EtOAc
  5. concentrationThe combined filtrates were concentrated
  6. customto give the product which
  7. customwas used without further purification

Sources & evidence

ORD record
ord-8191f7235c714ddbb17dc534d885c7d8
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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