HCID 12051828, compound → HCID 12051829, compound

HRID 2228607Notes

Reaction equation

HRID 2228607 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:9][C:10]([C:12]1[C:16]([CH3:17])=[C:15]([C:18]2[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=2)[N:14]([CH2:24][O:25][CH3:26])[C:13]=1[C:27]1[CH:32]=[CH:31][N:30]=[CH:29][CH:28]=1)=O)C>[Cl-].[NH4+]>[OH:9][CH2:10][C:12]1[C:16]([CH3:17])=[C:15]([C:18]2[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=2)[N:14]([CH2:24][O:25][CH3:26])[C:13]=1[C:27]1[CH:28]=[CH:29][N:30]=[CH:31][CH:32]=1

Participants

4

Reactant 2

HCID 12051828HCID 12051828, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 12051829HCID 12051829, compoundYield 75.6%

Reagents, catalysts & solvents 1

HCID 25517Ammonium ChlorideSolvent

Procedure

To a stirred suspension of lithium aluminum hydride (LAH) (88 mg, 2.31 mmol) was added 3-ethoxycarbonyl-1-methoxymethyl-4-methyl-2,5-di(4-pyridyl)-1H-pyrrole (270 mg, 0.77 mmol) at 0° C. under nitrogen. After stirring for 2 hours, the reaction mixture was allowed to warm to room temperature and stirred for 3 days. Saturated aqueous ammonium chloride solution (50 mL) was added to the mixture, and the whole was extracted with ethyl acetate (70 mL×2). Combined organic layers were washed. with brine (50 mL), dried over MgSO4, and concentrated il vacuo to afford the subtitle compound (180 mg, 5.8% yield) as a solid.

Workup

  1. stirringstirred for 3 days
  2. extractionthe whole was extracted with ethyl acetate (70 mL×2)
  3. washCombined organic layers were washed
  4. dry with materialwith brine (50 mL), dried over MgSO4
  5. concentrationconcentrated il vacuo

Sources & evidence

ORD record
ord-ef3583c7b1704014a323814c766fdadf
Source dataset
uspto-grants-2002_07
Patent number
US06417202B1

Reaction notes

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