HCID 19106928, compound → HCID 19106901, compound

HRID 1197593Notes

Reaction equation

HRID 1197593 reaction equation
[CH2:1]([C:5]1[NH:6][C:7]([C:15](OCC)=[O:16])=[C:8]([N:10]2[CH:14]=[CH:13][CH:12]=[CH:11]2)[N:9]=1)[CH2:2][CH2:3][CH3:4].[H-].[H-].[H-].[H-].[Li+].[Al+3]>O1CCCC1.CCOCC>[CH2:1]([C:5]1[NH:6][C:7]([CH2:15][OH:16])=[C:8]([N:10]2[CH:11]=[CH:12][CH:13]=[CH:14]2)[N:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 2

HCID 19106928HCID 19106928, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 19106901HCID 19106901, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of ethyl 2-butyl-4-(1H-pyrrol-1-yl)imidazole-5-carboxylate (Example 21, 0.5 g) in tetrahydrofuran (15 mL) was treated with a 1 M solution of LiAlH4 in ether (2.1 mL). The reaction was stirred overnight at room temperature then quenched by addition of saturated aqueous (NH4)2SO4. The resulting suspension was extracted three times with ethyl acetate and the combined organic layers were dried over anhydrous magnesium sulfate and evaporated to afford the title compound as an off-white solid. MS (DEI) 205 (m).

Workup

  1. customthen quenched by addition of saturated aqueous (NH4)2SO4
  2. extractionThe resulting suspension was extracted three times with ethyl acetate
  3. dry with materialthe combined organic layers were dried over anhydrous magnesium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-1afbd49e688c4abc84bf884ca4c2c5fd
Source dataset
uspto-grants-1994_01
Patent number
US05276048

Reaction notes

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