Aluminium lithium hydride → HCID 68247836, compound

HRID 1913522Notes

Reaction equation

HRID 1913522 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([CH:9]1[CH2:12][CH:11]([N:13]2[CH:17]=[C:16]([C:18](OCC)=[O:19])[N:15]=[CH:14]2)[CH2:10]1)[CH3:8]>O1CCCC1.C(OCC)C.S([O-])([O-])(=O)=O.[Na+].[Na+]>[CH2:7]([CH:9]1[CH2:10][CH:11]([N:13]2[CH:17]=[C:16]([CH2:18][OH:19])[N:15]=[CH:14]2)[CH2:12]1)[CH3:8]

Participants

6

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 71223162HCID 71223162, compound

Product 1

HCID 68247836HCID 68247836, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×HCID 24436Sodium SulfateSolvent

Conditions

Temperature
0 °C

Procedure

Lithium aluminum hydride (92%, 80 mg) was suspended in tetrahydrofuran (4 mL). To this suspension, a solution of ethyl 1-(3-ethylcyclobutyl)-1H-imidazole-4-carboxylate in tetrahydrofuran (5 mL) was slowly added dropwise at 0° C. After stirring at 0° C. for 30 minutes, the reaction solution was diluted with diethyl ether, and saturated aqueous sodium sulfate was added thereto. After stirring at room temperature for 1 hour, the formed inorganic salt was removed by filtration through celite. The filtrate was concentrated under reduced pressure to obtain a crude product. This crude product was purified by silica gel column chromatography (eluting solvent: methylene chloride-methylene chloride/methanol=5/1) to obtain the title compound (119 mg, diastereomeric mixture, trans:cis=1:1).

Workup

  1. additionwas added
  2. stirringAfter stirring at room temperature for 1 hour
  3. customthe formed inorganic salt was removed by filtration through celite
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customto obtain a crude product
  6. customThis crude product was purified by silica gel column chromatography (eluting solvent: methylene chloride-methylene chloride/methanol=5/1)

Sources & evidence

ORD record
ord-85843065ac604f3295352bc92aba79c6
Source dataset
uspto-grants-2013_12
Patent number
US08609710B2

Reaction notes

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